1,3-Propanediol

1,3-Propanediol is the organic compound with the formula CH2(CH2OH)2. This 3-carbon diol is a colorless viscous liquid that is miscible with water, and an ingredient in Jheri curl activator.[2]

1,3-Propanediol
Skeletal formula of 1,3-propanediol
Spacefill model of 1,3-propanediol
Names
Preferred IUPAC name
Propane-1,3-diol[1]
Other names
1,3-Dihydroxypropane
Trimethylene glycol
Identifiers
CAS Number
3D model (JSmol)
3DMet
Abbreviations PDO
Beilstein Reference
 969155
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.271
EC Number
  • 207-997-3
KEGG
MeSH 1,3-propanediol
PubChem CID
RTECS number
  • TY2010000
UNII
InChI
  • InChI=1S/C3H8O2/c4-2-1-3-5/h4-5H,1-3H2 Y
    Key: YPFDHNVEDLHUCE-UHFFFAOYSA-N Y
  • Key: YPFDHNVEDLHUCE-UHFFFAOYAS
SMILES
  • OCCCO
Properties
Chemical formula
 C3H8O2
Molar mass 76.095 g·mol−1
Appearance Colourless liquid
Density 1.0597 g cm−3
Melting point −27 °C; −17 °F; 246 K
Boiling point 211 to 217 °C; 412 to 422 °F; 484 to 490 K
Solubility in water
 Miscible
log P −1.093
Vapor pressure 4.5 Pa
Refractive index (nD)
 1.440
Thermochemistry
Std enthalpy of
formation (ΔfH⦵298)
 −485.9–−475.7 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 −1848.1–−1837.9 kJ mol−1
Hazards
NFPA 704 (fire diamond)
2
2
0
Flash point 79.444 °C (174.999 °F; 352.594 K)
Autoignition
temperature
 400 °C (752 °F; 673 K)
Safety data sheet (SDS) sciencelab.com
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Products

It is mainly used as a building block in the production of polymers such as polytrimethylene terephthalate.[3]

1,3-Propanediol can be formulated into a variety of industrial products including composites, adhesives, laminates, coatings, moldings, aliphatic polyesters, copolyesters. It is also a common solvent. It is used as an antifreeze and as a component in wood paint.

Production

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

Two other routes involve bioprocessing by certain micro-organisms:

  • Conversion from glucose effected by a genetically modified strain of E. coli by DuPont Tate & Lyle BioProducts (See: bioseparation of 1,3-propanediol). An estimated 120,000 tons were produced in 2007".[4] According to DuPont, the Bio-PDO process uses 40% less energy than conventional processes,[5][6] Because of DuPont and Tate & Lyle's success in developing a renewable Bio-PDO process, the American Chemical Society awarded the Bio-PDO research teams the "2007 Heroes of Chemistry" award.[6]
  • Conversion from glycerol (a by-product of biodiesel production) using Clostridium diolis bacteria and Enterobacteriaceae.[7]

Safety

1,3-Propanediol does not appear to pose a significant hazard via inhalation of either the vapor or a vapor/aerosol mixture.[8]

See also

References
  1. "1,3-propanediol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 20 October 2011.
  2. Merck Index, 11th Edition, 9629.
  3. Carl 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.
  4. Werle, Peter; Morawietz, Marcus; Lundmark, Stefan; Sörensen, Kent; Karvinen, Esko; Lehtonen, Juha (2008-07-15), Wiley-VCH Verlag GmbH & Co. KGaA (ed.), "Alcohols, Polyhydric", 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, retrieved 2022-03-31
  5. Carl F. Muska; Carina Alles (2005-05-11). "Biobased 1,3-Propanediol A New Platform Chemical For The 21st Century" (PDF). BREW Symposium.
  6. "Growing Demand for Products Manufactured from DuPont's Bio-Based Propanediol". AZoM.com. 2007-06-12.
  7. 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.
  8. 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.
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