1,3-Propanediol
Chemical compound
From Wikipedia, the free encyclopedia
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.
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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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| 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 | |||
| CH2(CH2OH)2 | |||
| Molar mass | 76.095 g·molâ1 | ||
| Appearance | Colourless liquid | ||
| Density | 1.0597 g cmâ3 | ||
| Melting point | â27 °C; â17 °F; 246 K | ||
| Boiling point | 211 to 217 °C; 412 to 422 °F; 484 to 490 K | ||
| Miscible | |||
| log P | â1.093 | ||
| Vapor pressure | 4.5 Pa | ||
Refractive index (nD) |
1.440 | ||
| Thermochemistry | |||
Std enthalpy of formation (ÎfH⦵298) |
â485.9ââ475.7 kJ molâ1 | ||
Std enthalpy of combustion (ÎcH⦵298) |
â1848.1ââ1837.9 kJ molâ1 | ||
| 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 | ||
| Related compounds | |||
Related glycols |
Ethylene glycol, 1,2-propanediol | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]