Chemistry:1,3-Propanediol
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| Names | |||
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| Preferred IUPAC name
Propane-1,3-diol[1] | |||
| Other names
1,3-Dihydroxypropane
Trimethylene glycol | |||
| Identifiers | |||
3D model (JSmol)
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| 3DMet | |||
| Abbreviations | PDO | ||
| 969155 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| DrugBank | |||
| EC Number |
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| KEGG | |||
| MeSH | 1,3-propanediol | ||
PubChem CID
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| RTECS number |
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| UNII | |||
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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 | |||
| Safety data sheet | sciencelab.com | ||
| NFPA 704 (fire diamond) | |||
| 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). | |||
 verify (what is   ?)
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| Infobox references | |||
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.
Products
It is mainly used as a building block in the production of polymers such as polytrimethylene terephthalate.[2]
1,3-Propanediol can be formulated into a variety of industrial products including composites, adhesives, laminates, coatings, moldings, aliphatic polyesters, and 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.[2]
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".[3] According to DuPont, the Bio-PDO process uses 40% less energy than conventional processes,[4][5] 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.[5]
- Conversion from glycerol (a by-product of biodiesel production) using Clostridium diolis bacteria and Enterobacteriaceae.[6]
Safety
1,3-Propanediol does not appear to pose a significant hazard via inhalation of either the vapor or a vapor/aerosol mixture.[7] However, like with any chemical exposure should be controlled and maintained.
See also
- Butylene glycol
- Ethylene glycol
- Polylactic acid
- Propylene glycol
References
- ↑ "1,3-propanediol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10442&loc=ec_rcs. Retrieved 20 October 2011.
- ↑ 2.0 2.1 Carl J. Sullivan; Anja Kuenz; Klaus-Dieter Vorlop (2018). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_163.pub2.
- ↑ Werle, Peter; Morawietz, Marcus; Lundmark, Stefan; Sörensen, Kent; Karvinen, Esko; Lehtonen, Juha (2008-07-15), Wiley-VCH Verlag GmbH & Co. KGaA, ed. (in en), Alcohols, Polyhydric, 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, https://onlinelibrary.wiley.com/doi/10.1002/14356007.a01_305.pub2, retrieved 2022-03-31
- ↑ "Biobased 1,3-Propanediol A New Platform Chemical For The 21st Century". BREW Symposium. 2005-05-11. http://www.chem.uu.nl/brew/BREWsymposiumWiesbaden11mei2005/WEBSITEBrewPresentations51105.PDF.
- ↑ 5.0 5.1 "Growing Demand for Products Manufactured from DuPont's Bio-Based Propanediol". AZoM.com. 2007-06-12. http://www.azom.com/news.aspx?NewsID=8862.
- ↑ 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.
- ↑ "Inhalation toxicity of 1,3-propanediol in the rat". Inhal Toxicol 17 (9): 487–93. 2005. doi:10.1080/08958370590964485. PMID 16020043.
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