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{{Short description|Organic compound ethane-1,2-diol}} |
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{{Chembox |
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{{distinguish|text=], ], ], or ]}}{{Chembox |
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| verifiedrevid = 408945455 |
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| Verifiedfields = changed |
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| ImageFileL1 = Ethylene glycol chemical structure.png |
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| Watchedfields = changed |
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| ImageNameL1 = Wireframe model of ethylene glycol |
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| verifiedrevid = 457630599 |
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| ImageFileR1 = Ethylene-glycol-3D-vdW.png |
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| Name = |
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| ImageNameR1 = Spacefill model of ethylene glycol |
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| ImageFile = |
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| ImageFile2 = Ethylene-glycol-3D-balls.png |
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| ImageName2 = Ball and stick model of ethylene glycol |
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| ImageFile1 = Ethylene glycol.svg |
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| ImageName1 = Wireframe model of ethylene glycol |
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| IUPACName = Ethan-1,2-diol |
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| ImageFileL2 = Ethylene-glycol-3D-vdW.png |
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| OtherNames = 1,2-Ethanediol<br /> |
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| ImageNameL2 = Spacefill model of ethylene glycol |
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Glycol<br /> |
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| ImageFileR2 = Ethylene-glycol-3D-balls.png |
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Ethylene Alcohol<br /> |
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| ImageNameR2 = Ball and stick model of ethylene glycol |
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Hypodicarbonous acid<br /> |
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| ImageFile3 = Samlpe of Ethylene glycol.jpg |
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Monoethylene glycol |
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| ImageName3 = Sample of ethylene glycol |
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| Section1 = {{Chembox Identifiers |
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| PIN = Ethane-1,2-diol<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=690 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> |
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| Abbreviations = MEG |
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| OtherNames = {{ubl|Ethylene glycol|1,2-Ethanediol|Ethylene alcohol|Hypodicarbonous acid|Monoethylene glycol|1,2-Dihydroxyethane|Glycol solvent}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| IUPACName = Ethylene glycol<ref>{{cite web | url=https://www.ebi.ac.uk/chebi/searchId.do?chebiId=30742 | title=Ethylene glycol (CHEBI:30742) }}</ref><br>Ethane-1,2-diol<ref>{{cite web | url=https://www.ebi.ac.uk/chebi/searchId.do?chebiId=30742 | title=Ethylene glycol (CHEBI:30742) }}</ref> |
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| Section1 = {{Chembox Identifiers |
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| Abbreviations = MEG |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 457299 |
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| ChEMBL = 457299 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = LYCAIKOWRPUZTN-UHFFFAOYSA-N |
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| StdInChIKey = LYCAIKOWRPUZTN-UHFFFAOYSA-N |
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| CASNo = 107-21-1 |
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| CASNo = 107-21-1 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 104700-12-1 |
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| PubChem = 174 |
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| ChemSpiderID = 13835235 |
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| CASNo1_Comment = (<sup>13</sup>''C''<sub>2</sub>) |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo2 = 59609-67-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo2_Comment = (<sup>14</sup>''C''<sub>2</sub>) |
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| CASNo3 = 2219-52-5 |
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| CASNo3_Comment = (<sup>2</sup>''H''),(<sup>2</sup>''H'') |
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| PubChem = 174 |
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| PubChem_Ref = {{Pubchemcite}} |
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| PubChem1 = 21334931 |
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| PubChem1_Comment = (1-<sup>2</sup>''H''<sub>1</sub>) |
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| PubChem1_Ref = {{Pubchemcite}} |
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| PubChem2 = 16213434 |
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| PubChem2_Comment = (<sup>13</sup>''C''<sub>2</sub>) |
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| PubChem2_Ref = {{Pubchemcite}} |
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| PubChem3 = 134462 |
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| PubChem3_Comment = (<sup>14</sup>''C''<sub>2</sub>) |
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| PubChem3_Ref = {{Pubchemcite}} |
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| PubChem4 = 10986148 |
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| PubChem4_Comment = (<sup>2</sup>''H''),(<sup>2</sup>''H'') |
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| PubChem4_Ref = {{Pubchemcite}} |
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| ChemSpiderID = 13835235 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID1 = 13835235 |
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| ChemSpiderID1_Comment = (<sup>13</sup>''C''<sub>2</sub>) |
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| ChemSpiderID1_Ref = {{Chemspidercite}} |
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| ChemSpiderID2 = 118525 |
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| ChemSpiderID2_Comment = (<sup>14</sup>''C''<sub>2</sub>) |
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| ChemSpiderID2_Ref = {{Chemspidercite}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = FC72KVT52F |
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| UNII = FC72KVT52F |
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| EINECS = 203-473-3 |
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| EINECS = 203-473-3 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank = <!-- blanked - oldvalue: DB01867 --> |
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| DrugBank = |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D06424 |
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| KEGG = C01380 |
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| MeSHName = Ethylene+glycol |
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| MeSHName = Ethylene+glycol |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 30742 |
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| ChEBI = 30742 |
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| RTECS = KW2975000 |
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| RTECS = KW2975000 |
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| SMILES = C(CO)O |
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| UNNumber = 3082 |
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| InChI = 1/C2H6O2/c3-1-2-4/h3-4H,1-2H2 |
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| SMILES = OCCO |
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| InChI = 1/C2H6O2/c3-1-2-4/h3-4H,1-2H2 |
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| InChIKey = LYCAIKOWRPUZTN-UHFFFAOYAD |
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| InChIKey = LYCAIKOWRPUZTN-UHFFFAOYAD |
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| Beilstein = 505945 |
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| Beilstein = 505945 |
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| Gmelin = 943 |
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| Gmelin = 943 |
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| 3DMet = B00278}} |
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| 3DMet = B00278 |
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}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=2|H=6|O=2 |
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| Appearance = |
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| C=2 | H=6 | O=2 |
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| Appearance = colorless liquid |
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| Density = 1.1132 g/cm³ |
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| Odor = Odorless<ref name=PGCH/> |
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| Density = {{cvt|1.1132|g/cm3}} |
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| MeltingPtC = −12.9 |
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| MeltingPtC = −12.9 |
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| Melting_notes = |
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| MeltingPt_notes = |
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| BoilingPtC = 197.3 |
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| BoilingPtC = 197.3 |
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| Boiling_notes = |
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| BoilingPt_notes = |
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| Solubility = ] with water<br>in all proportions. |
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| Solubility = ] |
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| SolubleOther = Soluble in alcohols, ethyl acetate, THF, and dioxane. Miscible with DCM and slightly miscible with diethyl ether. Not miscible with toluene or hexanes. |
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| SolubleOther = |
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| Solvent = |
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| Solvent = |
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| VaporPressure = 7.99 Pa (20 °C)<ref name=PGCH/> |
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| LogP = |
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| Viscosity = 1.61{{e|-2}} Pa·s<ref>{{cite web|url=http://physics.info/viscosity/|title=Viscosity|first=Glenn|last=Elert|website=The Physics Hypertextbook|access-date=2007-10-02}}</ref> |
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| VaporPressure = |
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| Viscosity = 1.61 × 10<sup>−2</sup> N*s / m<sup>2</sup><ref>{{cite web|url=http://hypertextbook.com/physics/matter/viscosity/|title=Viscosity|first=Glenn|last=Elert|work=The Physics Hypertextbook|accessdate=2007-10-02}}</ref> |
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| HenryConstant = |
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| HenryConstant = |
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| AtmosphericOHRateConstant = |
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| AtmosphericOHRateConstant = |
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| pKa = |
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| pKa = |
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| pKb = }} |
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| pKb = |
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| LogP = -1.69<ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/107-21-1_329621.html|title=Ethylene glycol|website=www.chemsrc.com}}</ref> |
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| Section4 = {{Chembox Thermochemistry |
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}} |
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| DeltaHf = |
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| Section3 = |
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| Section4 = {{Chembox Thermochemistry |
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| DeltaHf = −460 kJ/mol |
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| DeltaHc = |
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| DeltaHc = |
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| Entropy = |
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| Entropy = 166.9 J/(mol·K) |
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| HeatCapacity = }} |
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| HeatCapacity = 149.5 J/(mol·K) |
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}} |
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| Section7 = {{Chembox Hazards |
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| Section5 = |
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| EUClass = Harmful ('''Xn''') |
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| EUIndex = |
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| Section6 = |
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| Section7 = {{Chembox Hazards |
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| MainHazards= It is extremely harmful to pets and children. If ingested, get medical help immediately. |
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| MainHazards= Harmful, produces poisonous ] when ingested, flammable |
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| NFPA-H = 3 |
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| NFPA-H = 2 |
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| NFPA-F = 1 |
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| NFPA-F = 1 |
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| NFPA-R = 1 |
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| NFPA-R = 0 |
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| NFPA-O = |
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| NFPA-S = |
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| RPhrases = {{R22}} {{R36}} |
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| GHSPictograms = {{GHS07}}{{GHS08}} |
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| GHSSignalWord = Warning |
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| SPhrases = {{S26}} {{S36}} {{S37}} {{S39}} {{S45}} {{S53}} |
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| HPhrases = {{H-phrases|302|373}} |
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| RSPhrases = |
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| PPhrases = {{P-phrases|260|264|270|301+312|302|314|330|501}} |
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| ExternalMSDS = |
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| ExternalSDS = |
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| FlashPt = 111°C (231.8°F) (closed cup) |
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| Autoignition = 410°C (770°F) |
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| ExploLimits = |
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| FlashPtC = 111 |
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| FlashPt_notes = closed cup |
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| PEL = }} |
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| AutoignitionPtC = 410 |
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| Section8 = {{Chembox Related |
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| ExploLimits = 3.2–15.2%<ref name=PGCH/> |
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| OtherFunctn = ]<br>]<br>]<br>] |
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| PEL = None<ref name=PGCH>{{PGCH|0272}}</ref> |
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| Function = ]s |
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| REL = None established<ref name=PGCH/> |
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| OtherCpds =}} |
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| IDLH = None<ref name=PGCH/> |
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}} |
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| Section8 = {{Chembox Related |
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| OtherFunction = {{ubl|]|]|]|]}} |
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| OtherFunction_label = ]s |
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| OtherCompounds = |
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}} |
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}} |
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}} |
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'''Ethylene glycol''' (]: ethane-1,2-diol) is an ] (a ]<ref>{{Cite web |date=2018-10-13 |title=3.8: 3.8 Alcohols - Classification and Nomenclature |url=https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Map%3A_Organic_Chemistry_(Wade)/03%3A_Functional_Groups_and_Nomenclature/3.08%3A_3.8_Alcohols_-__Classification_and_Nomenclature |access-date=2022-04-21 |website=Chemistry LibreTexts |language=en}}</ref>) with the formula {{chem2|(CH_{2}OH)_{2} }}. It is mainly used for two purposes: as a raw material in the manufacture of polyester fibers and for ] formulations. It is an odorless, colorless, flammable, viscous liquid. It has a sweet taste, but is ]. This molecule has been observed in outer space.<ref>{{cite journal |author1= J. M. Hollis |author2=F. J. Lovas |author3=P. R. Jewell |author4=L. H. Coudert | title = Interstellar Antifreeze: Ethylene Glycol| journal = The Astrophysical Journal | volume = 571|issue =1 | pages = L59–L62 | date = 2002-05-20 | doi = 10.1086/341148 | bibcode=2002ApJ...571L..59H|s2cid=56198291 | doi-access = }}</ref> |
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'''Ethylene glycol''' (]: ethan-1,2-diol) is an ] widely used as an ] ] and a precursor to polymers. In its pure form, it is an odorless, colorless, syrupy, sweet-tasting liquid. Ethylene glycol is toxic, and ingestion can result in death. |
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Ethylene glycol is not to be confused with ], a heavier ether ], or with ], a nontoxic ] ]. |
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== Production == |
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== Production == |
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===Industrial routes=== |
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=== Historical aspects and natural occurrence=== |
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Ethylene glycol is produced from ] (ethene), via the intermediate ]. Ethylene oxide reacts with ] to produce ethylene glycol according to the ] |
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Ethylene glycol was first prepared in 1859 by the ] chemist ] from ethylene glycol diacetate via ] with ] and, in 1860, from the ] of ]. There appears to have been no commercial manufacture or application of ethylene glycol prior to ], when it was synthesized from ] in Germany and used as a substitute for ] in the ] industry. |
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: {{chem2|C_{2}H_{4}O + H_{2}O -> HO\sCH_{2}CH_{2}\sOH}} |
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In the United States, semicommercial production of ethylene glycol via ] started in 1917. The first large-scale commercial glycol plant was erected in 1925 at ], by Carbide and Carbon Chemicals Co. (now ] Corp.). By 1929, ethylene glycol was being used by almost all ] manufacturers. |
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This ] can be ] by either ]s or ], or can occur at neutral ] under elevated temperatures. The highest yields of ethylene glycol occur at acidic or neutral pH with a large excess of water. Under these conditions, ethylene glycol yields of 90% can be achieved. The major byproducts are the oligomers ], ], and ]. The separation of these oligomers and water is energy-intensive. World production of ethylene glycol was ~20 Mt in 2010.<ref name="YueZhaoMa2012">{{cite journal | last1 = Yue | first1 = Hairong | last2 = Zhao | first2 = Yujun | last3 = Ma | first3 = Xinbin | last4 = Gong | first4 = Jinlong | title = Ethylene glycol: properties, synthesis, and applications | journal = Chemical Society Reviews | date = 2012 | volume = 41 | issue = 11 | page = 4218 | issn = 0306-0012 | eissn = 1460-4744 | doi = 10.1039/c2cs15359a | pmid = 22488259 }}</ref> |
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In 1937, Carbide started up the first plant based on Lefort's process for vapor-phase oxidation of ethylene to ethylene oxide. Carbide maintained a monopoly on the direct oxidation process until 1953, when the Scientific Design process was commercialized and offered for licenses. |
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A higher selectivity is achieved by the use of ]'s ]. In the OMEGA process, the ethylene oxide is first converted with ] ({{CO2}}) to ]. This ring is then hydrolyzed with a base catalyst in a second step to produce mono-ethylene glycol in 98% selectivity.<ref>Scott D. Barnicki, "Synthetic Organic Chemicals", in Handbook of Industrial Chemistry and Biotechnology edited by James A. Kent, New York : Springer, 2012. 12th ed. {{ISBN|978-1-4614-4259-2}}.</ref> The carbon dioxide is released in this step again and can be fed back into the process circuit. The carbon dioxide comes in part from ethylene oxide production, where a part of the ethylene is completely ]. |
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This molecule has been observed in outer space.<ref>{{cite journal|author =J. M. Hollis, F. J. Lovas, P. R. Jewell, L. H. Coudert | title = Interstellar Antifreeze: Ethylene Glycol| journal = ] | volume = 571|issue =1 | pages = L59–L62 | date = 2002-05-20 | doi = 10.1086/341148 | bibcode=2002ApJ...571L..59H}}</ref> |
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Ethylene glycol is produced from ] in countries with large coal reserves and less stringent environmental regulations. The oxidative carbonylation of methanol to ] provides a promising approach to the production of {{chem|C|1}}-based ethylene glycol.<ref>{{cite web |url=http://www.chemsystems.com/reports/search/docs/prospectus/stmc10_coal_meg.pdf |title=Coal to MEG, Changing the Rules of the Game |website=Nexant/Chemsystems |access-date=2016-08-08 |url-status=dead |archive-url=https://web.archive.org/web/20110714135349/http://www.chemsystems.com/reports/search/docs/prospectus/stmc10_coal_meg.pdf |archive-date=July 14, 2011 }} (PDF; 5,4 MB), 2011 Prospectus.</ref> Dimethyl oxalate can be converted into ethylene glycol in high yields (94.7%)<ref>{{cite patent |
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===Current methods=== |
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| country = EP |
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Ethylene glycol is produced from ] (ethene), via the intermediate ]. Ethylene oxide reacts with ] to produce ethylene glycol according to the ]: |
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| number = 046 983 |
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: C<sub>2</sub>H<sub>4</sub>O + H<sub>2</sub>O → HO–CH<sub>2</sub>CH<sub>2</sub>–OH |
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| status = |
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| title = Process for continuously preparing ethylene glycol |
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| pubdate = |
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| gdate = |
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| fdate = 1982-03-10 |
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| pridate = |
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| inventor = |
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| invent1 = S. Tahara et al. |
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| invent2 = |
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| assign1 = Ube Industries |
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| assign2 = |
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| class = |
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| url = |
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}} and H. T. Teunissen and C. J. Elsevier, ''Ruthenium catalyzed hydrogenation of dimethyl oxalate to ethylene glycol'', J. Chem. Soc., Chem. Commun., 1997, 667–668), {{doi|10.1039/A700862G}}.</ref> by ] with a copper catalyst:<ref>S. Zhang et al., ''Highly-Dispersed Copper-Based Catalysts from Cu–Zn–Al Layered Double Hydroxide Precursor for Gas-Phase Hydrogenation of Dimethyl Oxalate to Ethylene Glycol'', Catalysis Letters, Sept. 2012, '''142''' (9), 1121–1127, {{doi|10.1007/s10562-012-0871-8}}.</ref> |
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] |
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This ] can be ] by either ]s or ], or can occur at neutral ] under elevated temperatures. The highest yields of ethylene glycol occur at acidic or neutral pH with a large excess of water. Under these conditions, ethylene glycol yields of 90% can be achieved. The major byproducts are the ethylene glycol ]s ], ], and ]. About 6.7 billion kilograms are produced annually.<ref name=Ullmanns>Siegfried Rebsdat1 and Dieter Mayer "Ethylene Glycol” in Ullmann’s Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim.{{DOI|10.1002/14356007.a10_101}}.</ref> |
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Because the methanol is recycled, only carbon monoxide, hydrogen, and oxygen are consumed. One plant with a production capacity of {{val|200000|u=tons}} of ethylene glycol per year is in ], and a second plant in the Chinese province of ] with a capacity of {{val|250000|u=tons per year}} was scheduled for 2012.<ref>{{Cite web | url=http://www.icis.com/resources/news/2012/01/30/9527520/china-s-coal-based-chemicals-are-a-trade-off/ |title = China's coal-based chemicals are a trade-off |author=Clay Boswell |date=30 Jan 2012 |website=Independent Commodity Intelligence Services}}</ref> {{As of|2015}}, four plants in China with a capacity of {{val|200000|u=t/a}} each were operating, with at least 17 more to follow.<ref>{{Cite book |url=https://books.google.com/books?id=EPCeBgAAQBAJ&q=meg+china+synthesis+gas&pg=PA15 |title=Industrial Coal Gasification Technologies Covering Baseline and High-Ash Coal |isbn=9783527336906 |last1=Gräbner |first1=Martin |date=2014-11-24 |publisher=John Wiley & Sons}}</ref> |
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A higher selectivity is achieved by use of the ]. In the OMEGA process, the ethylene oxide is first converted with ] ({{CO2}}) to ] to then react with water in a second step to selectively produce mono-ethylene glycol. The carbon dioxide is released in this step again and can be fed back into the process circuit. The carbon dioxide comes in part from the ethylene oxide production, where a part of the ] is completely ]. |
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== Uses == |
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===Biological routes=== |
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Ethylene glycol can be produced by recycling its polymeric derivatives such a ].<ref>{{cite journal |doi=10.1021/acs.chemrev.2c00644 |title=Enzymes' Power for Plastics Degradation |date=2023 |last1=Tournier |first1=Vincent |last2=Duquesne |first2=Sophie |last3=Guillamot |first3=Frédérique |last4=Cramail |first4=Henri |last5=Taton |first5=Daniel |last6=Marty |first6=Alain |last7=André |first7=Isabelle |journal=Chemical Reviews |volume=123 |issue=9 |pages=5612–5701 |pmid=36916764 |url=https://hal.science/hal-04150645/file/Andre_Chemical_Reviews_HAL.pdf }}</ref> |
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The major end uses of ethylene glycol are to make ] melt, which accounted for 86% of total ethylene glycol consumption in 2009, and antifreeze, at around 7% of total consumption. Because this material is cheaply available, it finds many niche applications.<ref name=Ullmanns/> |
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=== Historical routes === |
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===Coolant and heat transfer agent=== |
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According to most sources, French chemist ] (1817–1884) first prepared ethylene glycol in 1856.<ref>{{cite journal | author = Adolphe Wurtz | author-link = Charles-Adolphe Wurtz | date = 1856 | url = http://gallica.bnf.fr/ark:/12148/bpt6k3000k/f203.image | title = Sur le glycol ou alcool diatomique |trans-title=On glycol or dibasic alcohol | journal = Comptes Rendus | volume = 43 | pages = 199–204}}</ref> He first treated "ethylene iodide" (]) with silver acetate and then hydrolyzed the resultant "ethylene diacetate" with ]. Wurtz named his new compound "glycol" because it shared qualities with both ] (with one hydroxyl group) and ] (with three hydroxyl groups).<ref>Wurtz (1856), page 200: ''"… je propose de le nommer ''glycol'', parce qu'il se rapproche à la fois, par ses propriétés, de l'alcool proprement dit et de la glycérin, entre lesquels il se trouve placé."'' ( … I propose to call it ''glycol'' because, by its properties, it is simultaneously close to alcohol properly called and glycerin, between which it is placed.)</ref> In 1859, Wurtz prepared ethylene glycol via the ] of ].<ref>Ad. Wurtz (1859) (Synthesis of glycol from ethylene oxide and water), ''Comptes rendus'', '''49''' : 813–815.</ref> There appears to have been no commercial manufacture or application of ethylene glycol prior to ], when it was synthesized from ] in Germany and used as a substitute for ] in the ] industry. |
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The major use of ethylene glycol is as a medium for ] in, for example, automobiles and liquid cooled computers. Ethylene glycol is also commonly used in chilled water ] systems that place either the chiller or air handlers outside, or systems that must cool below the freezing temperature of water. In ]/cooling systems, ethylene glycol is the ] that transports heat through the use of a ]. The ethylene glycol either gains energy from the source (lake, ocean, ]) or dissipates heat to the source, depending if the system is being used for heating or cooling. |
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In the United States, semicommercial production of ethylene glycol via ] started in 1917. The first large-scale commercial glycol plant was erected in 1925 at ], by Carbide and Carbon Chemicals Co. (now ] Corp.). By 1929, ethylene glycol was being used by almost all ] manufacturers. In 1937, Carbide started up the first plant based on Lefort's process for vapor-phase oxidation of ethylene to ethylene oxide. Carbide maintained a monopoly on the direct oxidation process until 1953 when the Scientific Design process was commercialized and offered for licensing. |
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Pure ethylene glycol has a specific heat capacity about one half that of water. So, while providing freeze protection and an increased boiling point, ethylene glycol lowers the specific heat capacity of water mixtures relative to pure water. A 50/50 mix by mass has a specific heat capacity of about 0.75 BTU/lb F, thus requiring increased flow rates in same system comparisons with water. Additionally, the increase in boiling point over pure water inhibits nucleate boiling on heat transfer surfaces thus reducing heat transfer efficiency in some cases, such as gasoline engine cylinder walls. Therefore, pure ethylene glycol should not be used as an engine coolant in most cases. |
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== Uses == |
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===Coolant and heat-transfer agent=== |
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The major use of ethylene glycol is as an antifreeze agent in the ] in for example, automobiles and ] systems that either place the ] or ] outside or must cool below the freezing temperature of water. In ]/cooling systems, ethylene glycol is the ] that transports heat through the use of a ]. The ethylene glycol either gains energy from the source (lake, ocean, ]) or dissipates heat to the sink, depending on whether the system is being used for heating or cooling. |
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Pure ethylene glycol has a ] about one half that of water. So, while providing freeze protection and an increased boiling point, ethylene glycol lowers the specific heat capacity of water mixtures relative to pure water. A 1:1 mix by mass has a specific heat capacity of about 3140 J/(kg·°C) (0.75 BTU/(lb·°F)), three quarters that of pure water, thus requiring increased flow rates in same-system comparisons with water. |
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===Antifreeze=== |
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Due to its low freezing point and tendency to form ]es, ethylene glycol resists freezing. A mixture of 60% ethylene glycol and 40% water does not freeze until temperatures below −45 °C (−49°F).<ref name=Ullmanns/> Diethyleneglycol behaves similarly. It is used as a ] fluid for ]s and aircraft. The ] capabilities of ethylene glycol have made it an important component of ] (anticrystallization) mixtures for low-temperature preservation of biological tissues and organs. |
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The mixture of ethylene glycol with water provides additional benefits to coolant and antifreeze solutions, such as preventing corrosion and acid degradation, as well as inhibiting the growth of most microbes and fungi.<ref>{{Cite web|url=http://www.hydratechglobal.net/technical/Ethylene+Glycol/58/en|title=Hydratech - Specialist Fluid Solutions|website=www.hydratechglobal.net|access-date=2020-02-24|archive-date=2021-05-14|archive-url=https://web.archive.org/web/20210514041855/http://www.hydratechglobal.net/technical/Ethylene+Glycol/58/en|url-status=dead}}</ref> Mixtures of ethylene glycol and water are sometimes informally referred to in industry as glycol concentrates, compounds, mixtures, or solutions. |
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Ethylene glycol disrupts hydrogen bonding when dissolved in water. Pure ethylene glycol freezes at about −12°C (10.4°F), but when mixed with water molecules, neither can readily form a solid crystal structure, and therefore the freezing point of the mixture is depressed significantly. The minimum freezing point is observed when the ethylene glycol percent in water is about 70%, as shown below. This is the reason pure ethylene glycol is not used as an antifreeze—water is a necessary component as well. |
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Table of thermal and physical properties of saturated liquid ethylene glycol:<ref>{{Cite book |last=Holman |first=Jack P. |title=Heat Transfer |publisher=McGraw-Hill Companies, Inc |year=2002 |isbn=9780072406559 |edition=9th |location=New York, NY |pages=600–606 |language=English}}</ref><ref>{{Cite book |author=Frank P. Incropera, David P. Dewitt, heodore L. Bergman, Adrienne S. Lavigne |title=Fundamentals of Heat and Mass Transfer |publisher=John Wiley and Sons, Inc. |year=2007 |isbn=9780471457282 |edition=6th |location=Hoboken, NJ |pages=941–950 |language=English}}</ref> |
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{| class="wikitable" border="1" style="margin:1em auto;text-align:center;" |
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{|class="wikitable mw-collapsible" |
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|+ '''''' |
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!Temperature (°C) |
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|- |
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!Density (kg/m<sup>3</sup>) |
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! Weight Percent EG (%) |
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!Specific heat (kJ/(kg·K)) |
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! Freezing Point (deg F) |
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!Kinematic viscosity (m<sup>2</sup>/s) |
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! Freezing Point (deg C) |
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!Conductivity (W/(m⋅K)) |
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!Thermal diffusivity (m<sup>2</sup>/s) |
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!Prandtl Number |
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!Thermal expansivity (K<sup>−1</sup>) |
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|- |
|
|- |
|
| 0 |
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|0 |
|
|
|1130.75 |
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| 32 |
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|
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|2.294 |
|
| 0 |
|
|
|
|{{val|7.53E-5}} |
|
|
|0.242 |
|
|
|{{val|9.34E-8}} |
|
|
|615 |
|
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|{{val|6.50E-4}} |
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|- |
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|- |
|
|
|20 |
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| 10 |
|
|
|
|1116.65 |
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| 25 |
|
|
|
|2.382 |
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| -4 |
|
|
|
|{{val|1.92E-5}} |
|
|
|0.249 |
|
|
|{{val|9.39E-8}} |
|
|
|204 |
|
|
|{{val|6.50E-4}} |
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|- |
|
|- |
|
|
|40 |
|
| 20 |
|
|
|
|1101.43 |
|
| 20 |
|
|
|
|2.474 |
|
| -7 |
|
|
|
|{{val|8.69E-6}} |
|
|
|0.256 |
|
|
|{{val|9.39E-8}} |
|
|
|93 |
|
|
|{{val|6.50E-4}} |
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|- |
|
|- |
|
|
|60 |
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| 30 |
|
|
|
|1087.66 |
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| 5 |
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|
|
|2.562 |
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| -15 |
|
|
|
|{{val|4.75E-6}} |
|
|
|0.26 |
|
|
|{{val|9.32E-8}} |
|
|
|51 |
|
|
|{{val|6.50E-4}} |
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|- |
|
|- |
|
|
|80 |
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| 40 |
|
|
|
|1077.56 |
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| -10 |
|
|
|
|2.65 |
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| -23 |
|
|
|
|{{val|2.98E-6}} |
|
|
|0.261 |
|
|
|{{val|9.21E-8}} |
|
|
|32.4 |
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|{{val|6.50E-4}} |
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|- |
|
|- |
|
|
|100 |
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| 50 |
|
|
|
|1058.5 |
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| -30 |
|
|
|
|2.742 |
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| -34 |
|
|
|
|{{val|2.03E-6}} |
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|- |
|
|
|
|0.263 |
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| 60 |
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|
|
|{{val|9.08E-8}} |
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| -55 |
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|
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|22.4 |
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| -48 |
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|
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|{{val|6.50E-4}} |
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|- |
|
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| 70 |
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| -60 |
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| -51 |
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|- |
|
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| 80 |
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| -50 |
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| -45 |
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|- |
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| 90 |
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| -20 |
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| -29 |
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|- |
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| 100 |
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| -10 |
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| -12 |
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|} |
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|} |
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===Anti-freeze=== |
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However, the boiling point for aqueous ethylene glycol increases monotonically with increasing ethylene glycol percentage. Thus, the use of ethylene glycol not only depresses the freezing point, but also elevates the boiling point such that the operating range for the heat transfer fluid is broadened on both ends of the temperature scale. The increase in boiling temperature is due to pure ethylene glycol having a much higher boiling point and lower ] than pure water; there is no chemical stabilization against boiling of the liquid phase at intermediate compositions, as there is against freezing. |
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Pure ethylene glycol freezes at about −12 °C (10.4 °F) but, when mixed with water, the mixture freezes at a lower temperature. For example, a mixture of 60% ethylene glycol and 40% water freezes at −45 °C (−49 °F).<ref name=Ullmanns>{{Ullmann | author1 = Siegfried Rebsdat | author2 = Dieter Mayer | title = Ethylene Glycol | doi = 10.1002/14356007.a10_101}}</ref> ] behaves similarly. The freezing point depression of some mixtures can be explained as a ] of solutions but, in highly concentrated mixtures such as the example, deviations from ideal solution behavior are expected due to the influence of ]. It's important to note that though pure and distilled water will have a greater specific heat capacity than any mixture of antifreeze and water, commercial antifreezes also typically contain an anti-corrosive additive to prevent pure water from corroding coolant passages in the engine block, cylinder head(s), water pump and radiator. |
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There is a difference in the mixing ratio, depending on whether it is ethylene glycol or propylene glycol. For ethylene glycol, the mixing ratios are typically 30/70 and 35/65, whereas the propylene glycol mixing ratios are typically 35/65 and 40/60. It is important that the mixture be frost-proof at the lowest operating temperature.<ref>{{Cite web|url=https://lcglad.dk/glycol/|title=Glycol til industri og erhverv|website=LC Glad|via=lcglad.dk|language=da|trans-title=Glycol for industry and business}}</ref> |
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{| class="wikitable" border="1" style="margin:1em auto;text-align:center;" |
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|+ '''''' |
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Because of the depressed freezing temperatures, ethylene glycol is used as a ] fluid for ]s and aircraft, as an ] in automobile engines, and as a component of ] (anticrystallization) mixtures for low-temperature preservation of biological tissues and organs. |
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|- |
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|
! Weight Percent EG (%) |
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The use of ethylene glycol not only depresses the freezing point of aqueous mixtures, but also elevates their boiling point. This results in the operating temperature range for heat-transfer fluids being broadened on both ends of the temperature scale. The increase in boiling temperature is due to pure ethylene glycol having a much higher boiling point and lower ] than pure water. |
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! Boiling Point (deg F) |
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! Boiling Point (deg C) |
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|- |
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| 0 |
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| 212 |
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| 100 |
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|- |
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| 10 |
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| 215 |
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| 102 |
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|- |
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| 20 |
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| 215 |
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| 102 |
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|- |
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| 30 |
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| 220 |
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| 104 |
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|- |
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| 40 |
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| 220 |
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| 104 |
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|- |
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| 50 |
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| 225 |
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| 107 |
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|- |
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| 60 |
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| 230 |
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| 110 |
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|- |
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| 70 |
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| 240 |
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| 116 |
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|- |
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| 80 |
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| 255 |
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| 124 |
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|- |
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| 90 |
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| 285 |
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| 140 |
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|- |
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| 100 |
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| 387 |
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| 197 |
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|} |
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===Precursor to polymers=== |
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===Precursor to polymers=== |
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], which is produced on the multimillion ton scale annually.]] |
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In the ]s industry, ethylene glycol is important precursor to ] fibers and ]s. ], used to make plastic bottles for ]s, is prepared from ethylene glycol. |
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In the ], ethylene glycol is an important precursor to ] fibers and ]s. ], used to make ]s for ]s, is prepared from ethylene glycol. |
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===Hydrate inhibition=== |
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===Other uses=== |
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====Dehydrating agent==== |
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Because of its high boiling point and affinity for water, ethylene glycol is a useful ]. Ethylene glycol is widely used to inhibit the formation of ] (hydrates) in long multiphase pipelines that convey natural gas from remote gas fields to an onshore processing facility. Ethylene glycol can be recovered from the natural gas and reused as an inhibitor after purification treatment that removes water and inorganic salts. |
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Ethylene glycol is used in the natural gas industry to remove water vapor from natural gas before further processing, in much the same manner as ] (TEG). |
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====Hydrate inhibition==== |
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Natural gas is dehydrated by ethylene glycol. In this application, ethylene glycol flows down from the top of a tower and meets a rising mixture of water vapor and ] gases. Dry gas exits from the top of the tower. The glycol and water are separated, and the glycol recycled. Instead of removing water, ethylene glycol can also be used to depress the temperature at which ] are formed. The purity of glycol used for hydrate suppression (monoethylene glycol) is typically around 80%, whereas the purity of glycol used for dehydration (triethylene glycol) is typically 95 to more than 99%. Moreover, the injection rate for hydrate suppression is much lower than the circulation rate in a glycol dehydration tower. |
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Because of its high boiling point and affinity for water, ethylene glycol is a useful ]. Ethylene glycol is widely used to inhibit the formation of ] (hydrates) in long multiphase pipelines that convey natural gas from remote gas fields to a gas processing facility. Ethylene glycol can be recovered from the natural gas and reused as an inhibitor after purification treatment that removes water and inorganic salts. |
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Natural gas is dehydrated by ethylene glycol. In this application, ethylene glycol flows down from the top of a tower and meets a rising mixture of water vapor and ] gases. Dry gas exits from the top of the tower. The glycol and water are separated, and the glycol recycled. Instead of removing water, ethylene glycol can also be used to depress the temperature at which ]s are formed. The purity of glycol used for hydrate suppression (monoethylene glycol) is typically around 80%, whereas the purity of glycol used for dehydration (triethylene glycol) is typically 95 to more than 99%. Moreover, the injection rate for hydrate suppression is much lower than the circulation rate in a ] tower. |
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===Niche applications=== |
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Minor uses of ethylene glycol include the manufacture of capacitors, as a chemical intermediate in the manufacture of ], and as an additive to prevent ] in liquid cooling systems for ]s. Ethylene glycol is also used in the manufacture of some ]s, but it is not itself present in these injections. It is used as a minor (1–2%) ingredient in ] and also in some inks and dyes. Ethylene glycol has seen some use as a rot and fungal treatment for wood, both as a preventative and a treatment after the fact. It has been used in a few cases to treat partially rotted wooden objects to be displayed in museums. It is one of only a few treatments that are successful in dealing with rot in wooden boats, and is relatively cheap. Ethylene glycol may also be one of the minor ingredients in screen cleaning solutions, along with the main ingredient ]. Ethylene glycol is commonly used as a ] for biological specimens, especially in secondary schools during ] as a safer alternative to ]. It can also be used in ]s. It is also used as part of the water-based fluid used to control subsea oil and gas production equipment. |
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====Precursor to other chemicals==== |
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==Chemical reactions== |
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Minor uses of ethylene glycol include the manufacture of capacitors, as a chemical intermediate in the manufacture of ], as an additive to prevent ] in liquid cooling systems for ]s, and inside the lens devices of cathode-ray tube type of rear projection televisions. Ethylene glycol is also used in the manufacture of some ]s, but it is not itself present in these injections. It is used as a minor (1–2%) ingredient in ] and also in some inks and dyes. Ethylene glycol has seen some use as a rot and fungal treatment for wood, both as a preventative and a treatment after the fact. It has been used in a few cases to treat partially rotted wooden objects to be displayed in museums. It is one of only a few treatments that are successful in dealing with rot in wooden boats, and is relatively cheap. Ethylene glycol may also be one of the minor ingredients in screen cleaning solutions, along with the main ingredient ]. Ethylene glycol is commonly used as a ] for biological specimens, especially in secondary schools during ] as a safer alternative to ]. It is also used as part of the water-based hydraulic fluid used to control subsea oil and gas production equipment. |
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Ethylene glycol is used as a ] for ]s in ]. Treating a ketone or aldehyde with ethylene glycol in the presence of an acid catalyst (e.g., ]; ]) gives the corresponding a 1,3-dioxolane, which is resistant to bases and other nucleophiles. The 1,3-dioxolane protecting group can thereafter be removed by further acid ].<ref name = greene>{{cite book | title = Protective Groups in Organic Synthesis | edition = Third | author = Theodora W. Greene, Peter G. M. Wuts | publisher = John Wiley & Sons | isbn = 0-471-16019-9 | pages = 312–322 | year = 1999}}</ref> In this example, ] was protected using ethylene glycol with p-toluenesulfonic acid in moderate yield. Water was removed by ] to shift the equilibrium to the right.<ref>{{cite journal | author = J. H. Babler, N. C. Malek and M. J. Coghlan | title = Selective hydrolysis of α,β- and β,γ-unsaturated ketals: method for deconjugation of β,β-disubstituted α,β-unsaturated ketones | year = 1978 | journal = ] | volume = 43 | issue = 9 | pages = 1821–1823 | doi = 10.1021/jo00403a047}}</ref> |
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===Organic building block=== |
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Although dwarfed by its use as a precursor to ]s, ethylene glycol is useful in more specialized areas of organic chemistry. |
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It serves as a ] in ] for manipulation of ] and aldehydes.<ref>{{cite web | url = http://www.synarchive.com/protecting-group/Aldehyde_Ketone_Ethylene_glycol_acetal | title = Ethylene glycol acetal | website = The Organic Synthesis Archive | publisher = synarchive.com}}</ref><ref name = greene>{{cite book | title = Protective Groups in Organic Synthesis | edition = Third |author1=Theodora W. Greene |author2=Peter G. M. Wuts | publisher = John Wiley & Sons | isbn = 978-0-471-16019-9 | pages = 312–322 | year = 1999}}</ref> In one example, ] was protected using ethylene glycol:<ref>{{cite journal |author1=J. H. Babler |author2=N. C. Malek |author3=M. J. Coghlan | title = Selective hydrolysis of α,β- and β,γ-unsaturated ketals: method for deconjugation of β,β-disubstituted α,β-unsaturated ketones | year = 1978 | journal = ] | volume = 43 | issue = 9 | pages = 1821–1823 | doi = 10.1021/jo00403a047}}</ref> |
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] |
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The glycol-derived ] of ] is a commercial fragrance ].<ref>{{cite book |doi=10.1002/14356007.t11_t02 |chapter=Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2016 |last1=Panten |first1=Johannes |last2=Surburg |first2=Horst |pages=1–45 |isbn=978-3-527-30673-2 }}</ref> |
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==Miscellaneous chemical reactions== |
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Silicon dioxide dissolves slowly in hot ethylene glycol in the presence of ] base to produce silicates.<ref name=Laine>{{cite journal|last1=Laine|first1=Richard M.|last2=Blohowiak|first2=Kay Youngdahl|last3=Robinson|first3=Timothy R.|last4=Hoppe|first4=Martin L.|last5=Nardi|first5=Paola|last6=Kampf|first6=Jeffrey|last7=Uhm|first7=Jackie|title=Synthesis of pentacoordinate silicon complexes from SiO<sub>2</sub>|journal=Nature|volume=353|date=17 October 1991|issue=6345|pages=642–644|doi=10.1038/353642a0|bibcode=1991Natur.353..642L|url=https://deepblue.lib.umich.edu/bitstream/2027.42/62810/1/353642a0.pdf|hdl=2027.42/62810|s2cid=4310228|hdl-access=free}}</ref> |
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== Toxicity == |
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== Toxicity == |
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{{main|ethylene glycol poisoning}} |
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{{main|Ethylene glycol poisoning}} |
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Ethylene glycol is moderately toxic with an oral ] = 786 mg/kg for humans.<ref>{{Cite web |
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Ethylene glycol has relatively high mammalian toxicity when ingested, roughly on par with ], with an oral ] = 786 mg/kg for humans.<ref>{{cite web |
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| author = Safety Officer in Physical Chemistry |
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| author = Safety Officer in Physical Chemistry |
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| title = Safety (MSDS) data for ethylene glycol |
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| title = Safety (MSDS) data for ethylene glycol |
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| publisher = Oxford University |
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| work = |
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| date = November 23, 2009 |
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| publisher = Oxford University |
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| url = http://msds.chem.ox.ac.uk/ET/ethylene_glycol.html |
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| date = November 23, 2009 |
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| access-date = December 30, 2009 |
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| url = http://msds.chem.ox.ac.uk/ET/ethylene_glycol.html |
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| accessdate = December 30, 2009 |
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| archive-date = December 14, 2011 |
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| archive-url = https://web.archive.org/web/20111214093006/http://msds.chem.ox.ac.uk/ET/ethylene_glycol.html |
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| url-status = dead |
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}}</ref> The major danger is due to its sweet ], which can attract children and animals. Upon ingestion, ethylene glycol is oxidized to ], which is, in turn, oxidized to ], which is ]. It and its toxic byproducts first affect the ], then the heart, and finally the kidneys. Ingestion of sufficient amounts is fatal if untreated.<ref>. National Institute for Occupational Safety and Health. Emergency Response Database. August 22, 2008. Retrieved December 31, 2008.</ref> Several deaths are recorded annually in the U.S. alone.<ref>{{EMedicine|article|814701|Ethylene Glycol Toxicity}}</ref> |
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Antifreeze products for automotive use containing ] in place of ethylene glycol are available. They are generally considered safer to use, as propylene glycol is not as palatable{{refn|group=note|Pure propylene glycol does not taste bitter, and pure propylene glycol is often used as a food additive, for instance in cake icing and shelf-stable whipped cream. Industrial-grade propylene glycol usually has a slightly bitter or acrid taste due to impurities. See the article on ] for more information. The relative sweetness of ethylene glycol<ref>{{cite book|title=The Merck Index|date=2013|publisher=Royal Society of Chemistry|pages=M5122|edition=15th}}</ref> and propylene glycol<ref>{{cite book|title=The Merck Index|date=2013|publisher=Royal Society of Chemistry|pages=M9238|edition=15th}}</ref> is discussed in the Merck Index, and neither compound is described as bitter.}} and is converted in the body to ], a normal product of metabolism and exercise.<ref>{{cite web |url=http://www.resteddoginn.ca/antifreeze.php |title=Ethylene Glycol Poisoning |author=Pieter Klapwijk |date=January 27, 2010 |publisher=The Rested Dog Inn |access-date=October 11, 2012 |archive-date=January 26, 2013 |archive-url=https://web.archive.org/web/20130126003300/http://www.resteddoginn.ca/antifreeze.php |url-status=dead }}</ref> |
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}}</ref> The major danger is due to its sweet taste. Because of that, children and animals are more inclined to consume large quantities of it than of other poisons. Upon ingestion, ethylene glycol is oxidized to ] which is, in turn, oxidized to ], which is toxic. It and its toxic byproducts first affect the ], then the heart, and finally the kidneys. Ingestion of sufficient amounts can be fatal if untreated.<ref>. National Institute for Occupational Safety and Health. Emergency Response Database. August 22, 2008. Retrieved December 31, 2008. |
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</ref> |
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Australia, the UK, and seventeen US states (as of 2012) require the addition of a bitter flavoring (]) to antifreeze. In December 2012, US antifreeze manufacturers agreed voluntarily to add a bitter flavoring to all antifreeze that is sold in the consumer market of the US.<ref>{{cite web|title=Antifreeze and Engine Coolant Being Bittered Nationwide|url=http://www.cspa.org/category/news-releases/2012/12/antifreeze-and-engine-coolant-being-bittered-nationwide/|publisher=Consumer Specialty Products Association|access-date=30 June 2016|archive-url=https://web.archive.org/web/20121228225407/http://www.cspa.org/news-media-center/news-releases/2012/12/antifreeze-and-engine-coolant-being-bittered-nationwide|archive-date=28 December 2012|date=13 December 2012}}</ref> |
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According to the annual report of the American Association of Poison Control Centers' National Poison Data System in 2007, |
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there were about 1000 total cases resulting in 16 deaths. |
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The 2008 American Association of Poison Control Centers' National Poison Data System annual report lists |
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7 deaths. |
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In 2022, several hundred children died of acute ] in ] and ] because the ] syrup made by ]-based Maiden Pharmaceuticals contained ethylene glycol and ], ingredients that have been linked to child deaths from ] in The Gambia.<ref>{{cite news |title=Indonesia says child deaths from acute kidney injury rise to 133 |url=https://www.aljazeera.com/news/2022/10/22/indonesia-says-child-deaths-from-acute-kidney-injury-rise-to-133 |work=] |date=22 October 2022}}</ref> In December 2022, ]'s health ministry has said children died as a result of ethylene glycol in ] made by ], which is based at ], near New Delhi.<ref>{{cite news |url=https://www.bbc.co.uk/news/world-asia-india-64114240 |title=Marion Biotech: Uzbekistan links child deaths to India cough syrup |date=29 December 2022 |work=] }}</ref> |
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== In the environment == |
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* The primary source of ethylene glycol in the environment is from run-off at airports where it is used in ] agents for runways and airplanes. Ethylene glycol can also enter the environment through the disposal of products that contain it. |
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* Ethylene glycol in air will break down in about 10 days. |
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* Ethylene glycol in water and in soil will break down within several days to a few weeks.<ref></ref> |
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==Environmental effects== |
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== References == |
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Ethylene glycol is a ]. It breaks down in air in about 10 days and in water or soil in a few weeks. It enters the environment through the dispersal of ethylene glycol-containing products, especially at airports, where it is used in ] agents for runways and airplanes.<ref>{{cite web|url = https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsDetails.aspx?faqid=85&toxid=21 |publisher = CDC|work = ToxFAQs|title = Ethylene Glycol|date = 12 March 2015}}</ref> While prolonged low doses of ethylene glycol show no toxicity, at near lethal doses (≥ 1000 mg/kg per day) ethylene glycol acts as a ]. "Based on a rather extensive database, it induces skeletal variations and malformations in rats and mice by all routes of exposure."<ref name=HC>{{cite web|title=Statement of the Science Report for Ethylene Glycol|url=http://www.hc-sc.gc.ca/ewh-semt/pubs/contaminants/psl2-lsp2/ethylene_glycol/index-eng.php#a2436 |website=3.3.2.2 Non-neoplastic effects|publisher=Health Canada www.hc-sc.gc.ca|access-date=27 August 2014|date=June 24, 2013}}</ref> |
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== Notes == |
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{{reflist|group=note}} |
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== References == |
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{{reflist}} |
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{{reflist}} |
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== External links == |
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== External links == |
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* {{cite journal |author1=Hairong Yue |author2=Yujun Zhao |author3=Xinbin Ma |author4=Jinlong Gong | title = Ethylene glycol: properties, synthesis, and applications | journal = Chemical Society Reviews | issue = 11 | year = 2012 | volume = 41 | pages = 4218–4244 | doi = 10.1039/C2CS15359A|pmid=22488259 }} |
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{{Alcohols}} |
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{{DEFAULTSORT:Ethylene Glycol}} |
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{{Automotive engine}} |
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{{Molecules detected in outer space}} |
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{{Authority control}} |
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{{DEFAULTSORT:Ethylene glycol}} |
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