1,3-Propanediol

1,3-Propanediol
IUPAC name

Propane-1,3-diol[1]
Other names

1,3-Dihydroxypropane
Trimethylene glycol
Identifiers
Abbreviations PDO
CAS number 504-63-2 Y
PubChem 10442
ChemSpider 13839553 Y
UNII 5965N8W85T Y
EC number 207-997-3
DrugBank DB02774
KEGG C02457 Y
MeSH 1,3-propanediol
ChEBI CHEBI:16109 Y
ChEMBL CHEMBL379652 N
RTECS number TY2010000
Beilstein Reference 969155
3DMet B00444
Jmol-3D images Image 1
Properties
Molecular formula C3H8O2
Molar mass 76.09 g mol−1
Exact mass 76.052429500 g mol−1
Appearance Colourless liquid
Density 1.0597 g cm−3
Melting point

59 °C, 332 K, 138 °F
Boiling point

211-217 °C, 484-490 K, 412-422 °F
Solubility in water Miscible
log P −1.093
Vapor pressure 4.5 Pa
Refractive index (nD) 1.440
Thermochemistry
Std enthalpy of
formation ΔfHo298		 −485.9–−475.7 kJ mol−1
Std enthalpy of
combustion ΔcHo298		 −1848.1–−1837.9 kJ mol−1
Hazards
MSDS sciencelab.com
S-phrases S23, S24/25
NFPA 704
2
1
0
Flash point 79.444 °C
Autoignition
temperature		 400 °C
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

1,3-Propanediol is the organic compound with the formula CH2(CH2OH)2. This three-carbon diol is a colorless viscous liquid that is miscible with water.[2]

Contents

Products

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

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 solvent and used as an antifreeze and wood paint.

Production

1,3-Propanediol may be chemically synthesized by the hydration of acrolein, or by the hydroformylation of ethylene oxide to afford 3-hydroxypropionaldehyde. The aldehyde is hydrogenated to give 1,3-propanediol.

Two other routes involve bioprocessing by certain micro-organisms:

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. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10442&loc=ec_rcs. Retrieved 20 October 2011. 
  2. ^ Merck Index, 11th Edition, 9629.
  3. ^ Peter Werle, Marcus Morawietz, Stefan Lundmark, Kent Sörensen, Esko Karvinen, Juha Lehtonen "Alcohols, Polyhydric" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2006, Weinheim.
  4. ^ a b http://www.chem.uu.nl/brew/BREWsymposiumWiesbaden11mei2005/WEBSITEBrewPresentations51105.PDF
  5. ^ a b c http://www.azom.com/News.asp?NewsID=8862
  6. ^ http://biopol.free.fr/?p=342
  7. ^ H. Biebl; K. Menzel, A.-P. Zeng and W.-D. Deckwer (1999). "Microbial production of 1,3-propanediol". Applied Microbiology and Biotechnology 52 (3): 289–297. doi:10.1007/s002530051523. PMID 10531640. 
  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. 

External links