1,3-Propanediol
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| Names | |||
|---|---|---|---|
| IUPAC name
Propane-1,3-diol[1]
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| Other names
1,3-Dihydroxypropane
Trimethylene glycol | |||
| Identifiers | |||
3D model (JSmol)
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| 3DMet | |||
| Abbreviations | PDO | ||
| 969155 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| DrugBank | |||
| ECHA InfoCard | 100.007.271 | ||
| EC Number |
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| KEGG | |||
| MeSH | 1,3-propanediol | ||
PubChem CID
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| RTECS number |
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| UNII | |||
CompTox Dashboard (EPA)
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| Properties | |||
| 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 | ||
| Miscible | |||
| log P | −1.093 | ||
| Vapor pressure | 4.5 Pa | ||
Refractive index (nD)
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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) | |||
| Flash point | 79.444 °C (174.999 °F; 352.594 K) | ||
| 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).
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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.[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 solvent and used as an antifreeze and 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 afford 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 corn syrup 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
- ^ "1,3-propanediol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 20 October 2011.
- ^ Merck Index, 11th Edition, 9629.
- ^ a b 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. ISBN 978-3527306732.
- ^ 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.
- ^ Carl F. Muska; Carina Alles (2005-05-11). "Biobased 1,3-Propanediol A New Platform Chemical For The 21st Century" (PDF). BREW Symposium.
- ^ a b "Growing Demand for Products Manufactured from DuPont's Bio-Based Propanediol". AZoM.com. 2007-06-12.
- ^ 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.
- ^ 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.