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1,3-Propanediol

From Wikipedia, the free encyclopedia
1,3-Propanediol
Skeletal formula of 1,3-propanediol
Skeletal formula of 1,3-propanediol
Spacefill model of 1,3-propanediol
Spacefill model of 1,3-propanediol
Ball and stick model of 1,3-propanediol
Ball and stick model of 1,3-propanediol
Names
Preferred IUPAC name
Propane-1,3-diol[1]
Other names
1,3-Dihydroxypropane
Trimethylene glycol
Identifiers
3D model (JSmol)
AbbreviationsPDO
969155
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.007.271Edit this at Wikidata
EC Number
  • 207-997-3
KEGG
MeSH1,3-propanediol
RTECS number
  • TY2010000
UNII
  • InChI=1S/C3H8O2/c4-2-1-3-5/h4-5H,1-3H2 checkY
    Key: YPFDHNVEDLHUCE-UHFFFAOYSA-N checkY
  • Key: YPFDHNVEDLHUCE-UHFFFAOYAS
  • OCCCO
Properties
CH2(CH2OH)2
Molar mass76.095 g·mol−1
AppearanceColourless liquid
Density1.0597 g cm−3
Melting point−27 °C; −17 °F; 246 K
Boiling point211 to 217 °C; 412 to 422 °F; 484 to 490 K
Miscible
logP−1.093
Vapor pressure4.5 Pa
1.440
Thermochemistry
−485.9–−475.7 kJ mol−1
−1848.1–−1837.9 kJ mol−1
Hazards
NFPA 704 (fire diamond)
Flash point79.444 °C (174.999 °F; 352.594 K)
400 °C (752 °F; 673 K)
Safety data sheet (SDS)sciencelab.com
Related compounds
Relatedglycols
Ethylene glycol,1,2-propanediol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

1,3-Propanediol is theorganic compound with theformulaCH2(CH2OH)2. This 3-carbondiol is a colorless viscous liquid that ismiscible with water.

Products

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It is mainly used as a building block in the production of polymers such aspolytrimethylene terephthalate.[2]

1,3-Propanediol can be formulated into a variety of industrial products includingcomposites,adhesives,laminates,coatings,moldings,aliphaticpolyesters, andcopolyesters. It is also a commonsolvent. It is used as anantifreeze and as a component inwood paint.

Production

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1,3-Propanediol is mainly produced by the hydration ofacrolein. An alternative route involves thehydroformylation ofethylene oxide to form 3-hydroxypropionaldehyde. The aldehyde is subsequently hydrogenated to give 1,3-propanediol. Biotechnological routes are also known.[2]

Two other routes involvebioprocessing by certain micro-organisms:

Safety

[edit]

1,3-Propanediol does not appear to pose a significant hazard via inhalation of either the vapor or a vapor/aerosol mixture.[7]

See also

[edit]

References

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  1. ^"1,3-propanediol - Compound Summary".PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved20 October 2011.
  2. ^abCarl J. Sullivan; Anja Kuenz; Klaus-Dieter Vorlop (2018). "Propanediols".Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.doi:10.1002/14356007.a22_163.pub2.ISBN 978-3-527-30673-2.
  3. ^Werle, Peter; Morawietz, Marcus; Lundmark, Stefan; Sörensen, Kent; Karvinen, Esko; Lehtonen, Juha (2008-07-15),"Alcohols, Polyhydric", in Wiley-VCH Verlag GmbH & Co. KGaA (ed.),Ullmann's Encyclopedia of Industrial Chemistry, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, pp. a01_305.pub2,doi:10.1002/14356007.a01_305.pub2,ISBN 978-3-527-30673-2, retrieved2022-03-31
  4. ^Carl F. Muska; Carina Alles (2005-05-11)."Biobased 1,3-Propanediol A New Platform Chemical For The 21st Century"(PDF). BREW Symposium.
  5. ^ab"Growing Demand for Products Manufactured from DuPont's Bio-Based Propanediol". AZoM.com. 2007-06-12.
  6. ^H. Biebl; K. Menzel; A.-P. Zeng; W.-D. Deckwer (1999). "Microbial production of 1,3-propanediol".Applied Microbiology and Biotechnology.52 (3):289–297.doi:10.1007/s002530051523.PMID 10531640.S2CID 20017229.
  7. ^Scott RS, Frame SR, Ross PE, Loveless SE, Kennedy GL (2005). "Inhalation toxicity of 1,3-propanediol in the rat".Inhal Toxicol.17 (9):487–93.doi:10.1080/08958370590964485.PMID 16020043.S2CID 25647781.

External links

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