Revision as of 14:13, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 470862332 of page 1,3-Propanediol for the Chem/Drugbox validation project (updated: 'KEGG'). |
Latest revision as of 11:20, 4 December 2024 edit 2409:40e0:103e:67c2:79c0:65d2:9d3d:1b03 (talk) Added section for related glycolsTags: Mobile edit Mobile web edit |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| verifiedrevid = 456364689 |
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| verifiedrevid = 477186003 |
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| ImageFile2 = 1,3-Propanediol-Ball&Stick.png |
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| ImageFile2 = 1,3-Propanediol-Ball&Stick.png |
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| ImageFile2_Ref = {{chemboximage|correct|??}} |
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| ImageFile2_Ref = {{chemboximage|correct|??}} |
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| ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| ImageNameR1 = Spacefill model of 1,3-propanediol |
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| ImageNameR1 = Spacefill model of 1,3-propanediol |
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| IUPACName = Propane-1,3-diol<ref>{{Cite web|title = 1,3-propanediol - Compound Summary|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10442&loc=ec_rcs|work = PubChem Compound|publisher = National Center for Biotechnology Information|accessdate = 20 October 2011|location = USA|date = 16 September 2004|at = Identification and Related Records}}</ref> |
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| PIN = Propane-1,3-diol<ref>{{Cite web|title = 1,3-propanediol - Compound Summary|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10442&loc=ec_rcs|work = PubChem Compound|publisher = National Center for Biotechnology Information|accessdate = 20 October 2011|location = USA|date = 16 September 2004|at = Identification and Related Records}}</ref> |
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| OtherNames = 1,3-Dihydroxypropane{{Citation needed|date = October 2011}}<br /> |
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| OtherNames = 1,3-Dihydroxypropane<br />Trimethylene glycol |
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|Section1={{Chembox Identifiers |
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Trimethylene glycol{{Citation needed|date = October 2011}} |
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| Abbreviations = PDO |
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| Section1 = {{Chembox Identifiers |
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| CASNo = 504-63-2 |
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| Abbreviations = PDO |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 504-63-2 |
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| Beilstein = 969155 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 10442 |
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| 3DMet = B00444 |
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| ChEBI = 16109 |
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| PubChem_Ref = {{Pubchemcite|correct|Pubchem}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChemSpiderID = 13839553 |
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| ChEMBL = 379652 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| UNII = 5965N8W85T |
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| ChemSpiderID = 13839553 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| EINECS = 207-997-3 |
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| DrugBank = DB02774 |
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| EINECS = 207-997-3 |
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| DrugBank = DB02774 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| KEGG = <!-- blanked - oldvalue: C02457 --> |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C02457 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| MeSHName = 1,3-propanediol |
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| MeSHName = 1,3-propanediol |
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| RTECS = TY2010000 |
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| PubChem = 10442 |
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| ChEBI = 16109 |
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| RTECS = TY2010000 |
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| UNII = 5965N8W85T |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChEMBL = 379652 |
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| StdInChI = 1S/C3H8O2/c4-2-1-3-5/h4-5H,1-3H2 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| RTECS = TY2010000 |
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| StdInChIKey = YPFDHNVEDLHUCE-UHFFFAOYSA-N |
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| Beilstein = 969155 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| 3DMet = B00444 |
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| InChIKey = YPFDHNVEDLHUCE-UHFFFAOYAS |
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| SMILES = OCCCO |
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| SMILES = OCCCO |
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| StdInChI = 1S/C3H8O2/c4-2-1-3-5/h4-5H,1-3H2 |
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}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|Section2={{Chembox Properties |
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| StdInChIKey = YPFDHNVEDLHUCE-UHFFFAOYSA-N |
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| Formula = {{chem2|CH2(CH2OH)2}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| C=3 | H=8 | O=2 |
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| InChIKey = YPFDHNVEDLHUCE-UHFFFAOYAS |
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| Appearance = Colourless liquid |
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| Density = 1.0597 g cm<sup>−3</sup> |
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| MeltingPtK = 246 |
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| BoilingPtK = 484 to 490 |
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| Solubility = Miscible |
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| LogP = −1.093 |
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| VaporPressure = 4.5 Pa |
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| RefractIndex = 1.440 |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section3={{Chembox Thermochemistry |
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| DeltaHf = −485.9–−475.7 kJ mol<sup>−1</sup> |
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| C = 3 |
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| DeltaHc = −1848.1–−1837.9 kJ mol<sup>−1</sup> |
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| H = 8 |
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| O = 2 |
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| ExactMass = 76.052429500 g mol<sup>−1</sup> |
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| Appearance = Colourless liquid |
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| Density = 1.0597 g cm<sup>−3</sup> |
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| MeltingPtK = 332 |
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| BoilingPtKL = 484 |
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| BoilingPtKH = 490 |
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| Solubility = Miscible |
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| LogP = −1.093 |
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| VaporPressure = 4.5 Pa |
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| RefractIndex = 1.440 |
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}} |
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}} |
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| Section3 = {{Chembox Thermochemistry |
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|Section4={{Chembox Hazards |
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| ExternalSDS = |
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| DeltaHf = −485.9–−475.7 kJ mol<sup>−1</sup> |
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| NFPA-H = 2 |
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| DeltaHc = −1848.1–−1837.9 kJ mol<sup>−1</sup> |
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| NFPA-F = 2 |
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| NFPA-R = 0 |
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| FlashPtC = 79.444 |
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| AutoignitionPtC = 400 |
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}} |
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| Section4 = {{Chembox Hazards |
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| Section8 = {{Chembox Related |
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| OtherFunction_label = ]s |
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| ExternalMSDS = |
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| OtherFunction = ], ] |
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| SPhrases = {{S23}}, {{S24/25}} |
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| NFPA-H = 1 |
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| NFPA-F = 2 |
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| NFPA-R = 0 |
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| FlashPt = 79.444 °C |
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| Autoignition = 400 °C |
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}} |
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'''1,3-Propanediol''' is the ] with the ] {{chem2|CH2(CH2OH)2}}. This 3-carbon ] is a colorless viscous liquid that is ] with water. |
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==Products== |
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It is mainly used as a building block in the production of polymers such as ].<ref name=Ullmann>{{Ullmann|title=Propanediols|author1=Carl J. Sullivan|author2=Anja Kuenz|author3=Klaus-Dieter Vorlop|year=2018|doi=10.1002/14356007.a22_163.pub2}}</ref> |
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1,3-Propanediol can be formulated into a variety of industrial products including ], ]s, ]s, ]s, ], ] ]s, and ]. It is also a common ]. It is used as an ] and as a component in ]. |
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==Production== |
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1,3-Propanediol is mainly produced by the hydration of ]. An alternative route involves the ] of ] to form 3-hydroxypropionaldehyde. The aldehyde is subsequently hydrogenated to give 1,3-propanediol. Biotechnological routes are also known.<ref name=Ullmann/> |
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Two other routes involve ] by certain micro-organisms: |
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* Conversion from ] effected by a ] ] of ] by ] (See: ]). An estimated 120,000 tons were produced in 2007".<ref>{{Citation |last1=Werle |first1=Peter |title=Alcohols, Polyhydric |date=2008-07-15 |url=https://onlinelibrary.wiley.com/doi/10.1002/14356007.a01_305.pub2 |encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry |pages=a01_305.pub2 |editor-last=Wiley-VCH Verlag GmbH & Co. KGaA |place=Weinheim, Germany |publisher=Wiley-VCH Verlag GmbH & Co. KGaA |language=en |doi=10.1002/14356007.a01_305.pub2 |isbn=978-3-527-30673-2 |access-date=2022-03-31 |last2=Morawietz |first2=Marcus |last3=Lundmark |first3=Stefan |last4=Sörensen |first4=Kent |last5=Karvinen |first5=Esko |last6=Lehtonen |first6=Juha}}</ref> According to DuPont, the Bio-PDO process uses 40% less energy than conventional processes,<ref name="chem.uu.nl">{{cite web | title = Biobased 1,3-Propanediol A New Platform Chemical For The 21st Century | author1 = Carl F. Muska | author2 = Carina Alles | publisher = BREW Symposium | date = 2005-05-11 | url = http://www.chem.uu.nl/brew/BREWsymposiumWiesbaden11mei2005/WEBSITEBrewPresentations51105.PDF}}</ref><ref name="azom.com">{{cite news | publisher = AZoM.com | url = http://www.azom.com/news.aspx?NewsID=8862 | title = Growing Demand for Products Manufactured from DuPont's Bio-Based Propanediol | date = 2007-06-12}}</ref> Because of DuPont and Tate & Lyle's success in developing a renewable Bio-PDO process, the ] awarded the Bio-PDO research teams the "2007 ]" award.<ref name="azom.com" /> |
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* Conversion from ] (a by-product of ] production) using '']'' bacteria and '']''.<ref>{{cite journal | title = Microbial production of 1,3-propanediol | author = H. Biebl |author2=K. Menzel|author3=A.-P. Zeng|author4=W.-D. Deckwer | journal = Applied Microbiology and Biotechnology | volume = 52 | pages = 289–297 | year = 1999 | pmid = 10531640 | doi = 10.1007/s002530051523 | issue = 3 | s2cid = 20017229}}</ref> |
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==Safety== |
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1,3-Propanediol does not appear to pose a significant hazard via inhalation of either the vapor or a vapor/aerosol mixture.<ref>{{cite journal | title = Inhalation toxicity of 1,3-propanediol in the rat |vauthors=Scott RS, Frame SR, Ross PE, Loveless SE, Kennedy GL | journal = ] | year = 2005 | volume = 17 | issue = 9 | pages = 487–93 | doi = 10.1080/08958370590964485 | pmid = 16020043|s2cid=25647781}}</ref> However, like with any chemical exposure should be controlled and maintained. |
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==See also== |
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* ] |
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* ] |
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* ] |
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* ] |
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==References== |
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{{Reflist}} |
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==External links== |
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* |
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{{DEFAULTSORT:Propandediol, 1, 3-}} |
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] |
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] |