1,3-Propanediol

1,3-Propanediol
Names
IUPAC name
Propane-1,3-diol[1]
Other names
1,3-Dihydroxypropane
Trimethylene glycol
Identifiers
504-63-2 YesY
3D model (Jmol) Interactive image
3DMet B00444
Abbreviations PDO
969155
ChEBI CHEBI:16109 YesY
ChEMBL ChEMBL379652 YesY
ChemSpider 13839553 YesY
DrugBank DB02774 YesY
ECHA InfoCard 100.007.271
EC Number 207-997-3
KEGG C02457 N
MeSH 1,3-propanediol
PubChem 10442
RTECS number TY2010000
UNII 5965N8W85T YesY
Properties
C3H8O2
Molar mass 76.10 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
Miscible
log P −1.093
Vapor pressure 4.5 Pa
1.440
Thermochemistry
−485.9–−475.7 kJ mol−1
−1848.1–−1837.9 kJ mol−1
Hazards
Safety data sheet 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
2
2
0
Flash point 79.444 °C (174.999 °F; 352.594 K)
400 °C (752 °F; 673 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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

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

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. Moreover, the bioconversion of glycerol to 1,3-propanediol is existent in certain bacteria.

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.[7]

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. 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. 1 2 Carl F. Muska; Carina Alles (2005-05-11). "Biobased 1,3-Propanediol A New Platform Chemical For The 21st Century" (PDF). BREW Symposium.
  5. 1 2 3 "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

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