gamma-Valerolactone
| gamma-Valerolactone[1] | |
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5-Methyldihydrofuran-2(3H)-one |
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Other names
4-Pentanolide, |
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| Identifiers | |
| CAS number | 108-29-2  |
| PubChem | 7921 |
| ChemSpider | 7633 |
| UNII | O7056XK37X |
| ChEBI | CHEBI:48569 |
| ChEMBL | CHEMBL195593 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C5H8O2 |
| Molar mass | 100.116 |
| Appearance | colorless liquid |
| Density | 1.0465 g/mL |
| Melting point |
-31 °C, 242 K, -24 °F |
| Boiling point |
207–208 °C |
| Solubility in water | >=100 mg/mL |
| Thermochemistry | |
| Std enthalpy of formation ΔfH |
-461.3 kJ·mol−1 |
| Std enthalpy of combustion ΔcH |
-2649.6 kJ·mol−1 |
| Hazards | |
| R-phrases | R36, R37, R38 |
| S-phrases | (S2), S46 |
| NFPA 704 |
 2
2
0
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| Flash point | 81 °C (178 °F) |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
gamma-Valerolactone (GVL) is an organic compound with the formula C5H8O2. This colourless liquid is one of the more common lactones. GVL is chiral but is usually used as the racemate. It is readily obtained from cellulosic biomass and is a potential fuel and green solvent.
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Synthesis [edit]
GVL is produced from levulinic acid, which is obtained from hexoses. In a typical process, cellulosic biomasses, such as corn stover, sawgrass, or wood, is hydrolysed into glucose and other sugars using acid catalysts. The resulting glucose can then be dehydrated via hydroxymethylfurfural to yield formic acid and levulinic acid, which can then be hydrogenated to gamma-hydroxypentanoic acid, which readily cyclises to gamma-valerolactone, which has potential applications as a liquid fuel.[2]
Potential applications [edit]
GVL has been identified as a potential green solvent. Because of its herbal odor, it is used in the perfume and flavor industries.[3] It is a structural isomer of delta-valerolactone.
Potential fuel [edit]
Since it is readily obtained from glucose, GVL has long been identified as a potential "green fuel."[4] GVL retains 97% of the energy of glucose and can be blended by itself in gasoline where it performs comparably to ethanol/gasoline mixtures.[5][6] However, due to blending limits for use in conventional combustion engines, it may be more efficient to convert GVL into liquid alkenes (or alkanes). The first step in this process is the ring-opening of GVL to yield a mixture of pentenoic acids. These acids can then be decarboxylated to produce butene and CO2. These conversions can be performed with zeolite catalysts.[7] After this stream is dehydrated, the products can be oligomerized at elevated pressures in the presence of a common acid-catalyst to yield alkenes with higher molecular weights, targeted for gasoline and other fuel applications.[8]
One of the main advantages that allows GVL to be a practical biofuel is that it is relatively inexpensive to produce. Using a cheap feedstock, this biofuel can be produced at prices between 2-3 US$/gallon.[5] The conversion of GVL to transportation fuel capable alkenes only requires a system containing two flow reactors, two phase separators, and a simple pumping arrangement for the delivery of an aqueous GVL feed. Since the use of precious metal catalysts is not required, this also decreases the total price of fuel production.[7]
See also [edit]
References [edit]
- ^ NIH National Toxicology Program
- ^ Huber, George W.; Iborra, Sara; Corma, Avelino (2006). "Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering". Chemical Reviews 106: 4044–4098. doi:10.1021/cr068360d.
- ^ GoodScentsCompany.com
- ^ Huber, G. W.; Corma, A. Angewandte Chemie International Edition 2007, 46, 7184. doi:10.1002/anie.200604504
- ^ a b Savage, Neil (2011). "Fuel Options: The Ideal Biofuel". Nature 474: S11. doi:10.1038/474S09a.
- ^ Horváth, I. T.; Mehdi, H.; Fábos, V.; Boda, L.; Mika, L. T. (2008). "γ-Valerolactone—a sustainable liquid for energy and carbon-based chemicals". Green Chemistry 10 (2): 238. doi:10.1039/b712863k.
- ^ a b Bond, David; Alonso; Wang, Dong; West, Ryan; Dumesic, James (2010). "Integrated Catalytic Conversion of γ-Valerolactone to Liquid Alkenes for Transportation Fuels". Science 357: 1110–1114. doi:10.1126/science.1184362.
- ^ Mantilla, A.; et al. (2005). "Oligomerization of isobutene on sulfated titania: Effect of reaction conditions on selectivity". Catalysis Today. 107-108: 707.
External links [edit]
- General Safety Information
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