1,3-Propanediol
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| Names | |||
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| IUPAC name
Propane-1,3-diol[1]
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| Other names
1,3-Dihydroxypropane
Trimethylene glycol |
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| Identifiers | |||
504-63-2  |
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| 3DMet | B00444 | ||
| Abbreviations | PDO | ||
| 969155 | |||
| ChEBI | CHEBI:16109 |
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| ChEMBL | ChEMBL379652 |
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| ChemSpider | 13839553 |
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| DrugBank | DB02774 |
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| EC Number | 207-997-3 | ||
| Jmol 3D model | Interactive image | ||
| KEGG | C02457  |
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| MeSH | 1,3-propanediol | ||
| PubChem | 10442 | ||
| RTECS number | TY2010000 | ||
| UNII | 5965N8W85T |
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| 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 | ||
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Refractive index (nD)
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1.440 | ||
| Thermochemistry | |||
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Std enthalpy of
formation (ΔfH |
−485.9–−475.7 kJ mol−1 | ||
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Std enthalpy of
combustion (ΔcH |
−1848.1–−1837.9 kJ mol−1 | ||
| Vapor pressure | {{{value}}} | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| 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] <templatestyles src="Module:Hatnote/styles.css"></templatestyles>
- 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]
See also
References
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 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 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 5.0 5.1 5.2 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
