1,3-Propanediol

From Wikipedia, the free encyclopedia
Jump to: navigation, search
1,3-Propanediol
Skeletal formula of 1,3-propanediol Spacefill model of 1,3-propanediol
Ball and stick model of 1,3-propanediol
Identifiers
Abbreviations PDO
CAS number 504-63-2 YesY
PubChem 10442
ChemSpider 13839553 YesY
UNII 5965N8W85T YesY
EC number 207-997-3
DrugBank DB02774
KEGG C02457 N
MeSH 1,3-propanediol
ChEBI CHEBI:16109 YesY
ChEMBL CHEMBL379652 YesY
RTECS number TY2010000
Beilstein Reference 969155
3DMet B00444
Jmol-3D images Image 1
Properties
Molecular formula C3H8O2
Molar mass 76.09 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
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
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 79.444 °C (174.999 °F; 352.594 K)
Autoignition temperature 400 °C (752 °F; 673 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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]

Products[edit]

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 in wood paint.

Production[edit]

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[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[edit]

  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. ^ 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 Carl F. Muska; Carina Alles (2005-05-11). "Biobased 1,3-Propanediol A New Platform Chemical For The 21st Century". BREW Symposium. 
  5. ^ a b c "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. 
  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. 

External links[edit]