GVL

gamma-Valerolactone[1]
Identifiers
CAS number 108-29-2 YesY
PubChem 7921
ChemSpider 7633 YesY
UNII O7056XK37X YesY
ChEBI CHEBI:48569 YesY
Jmol-3D images Image 1
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
ΔfHo298
-461.3 kJ·mol−1
Std enthalpy of
combustion
ΔcHo298
-2649.6 kJ·mol−1
Hazards
R-phrases R36, R37, R38
S-phrases (S2), S46
NFPA 704
2
2
0
Flash point 81 °C (178 °F)
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

Synthesis

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

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

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

References

External links

General Safety Information
  • gamma-Valerolactone MSDS by Sciencelab.com