1,3-Propanediol
| 1,3-Propanediol | |
|---|---|
 |
 |
 | |
| Propane-1,3-diol[1] | |
| Other names 1,3-Dihydroxypropane | |
| Identifiers | |
| Abbreviations | PDO |
| CAS number | 504-63-2  |
| PubChem | 10442 |
| ChemSpider | 13839553 |
| UNII | 5965N8W85T |
| EC number | 207-997-3 |
| DrugBank | DB02774 |
| KEGG | C02457  |
| MeSH | 1,3-propanediol |
| ChEBI | CHEBI:16109 |
| ChEMBL | CHEMBL379652 |
| 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 ΔfH |
−485.9–−475.7 kJ mol−1 |
| Std enthalpy of combustion ΔcH |
−1848.1–−1837.9 kJ mol−1 |
| Hazards | |
| MSDS | sciencelab.com |
| S-phrases | S23, S24/25 |
| NFPA 704 |
 2
2
0
|
| Flash point | 79.444 °C; 174.999 °F; 352.594 K |
| Autoignition temperature | 400 °C; 752 °F; 673 K |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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]
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.
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".[3] According to DuPont, the Bio-PDO process uses 40% less energy than conventional processes,[4][5] and reduces greenhouse gas emissions by 20%.,[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] See also: Bioseparation of 1,3-propanediol
- Conversion from glycerol (a by-product of biodiesel production) using Clostridium diolis bacteria and Enterobacteriaceae.[6][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.
- ↑ 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.
- ↑ 4.0 4.1 http://www.chem.uu.nl/brew/BREWsymposiumWiesbaden11mei2005/WEBSITEBrewPresentations51105.PDF
- ↑ 5.0 5.1 5.2 http://www.azom.com/News.asp?NewsID=8862
- ↑ http://biopol.free.fr/?p=342
- ↑ 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.
- ↑ 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.