108-29-2

Basic information

• Product Name: gamma-Valerolactone
• Synonyms: GAMMA-VALEROLACTONE NATURAL;gamma-Valerolactone, 98+%;γ-Methyl-γ-butyrolactone, 4,5-Dihydro-5-methyl-2(3H)-furanone, 4-Hydroxypentanoic acid lactone;γ-Methyl-γ-butyrolactone, (±)-γ-Valerolactone, 4,5-Dihydro-5-methyl-2(3H)-furanone, 4-Hydroxypentanoic acid lactone;4,5-Dihydro-5-methyl-2(3H)-franone;γ-Valeroactone;^y-Valerolactone, 98+%;γ-Valerolactone >= 99.0%, Natural, FCC
• CAS NO: 108-29-2
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.12
• EINECS: 203-569-5
• Product Categories: lactone flavors;Food Additive;Fatty & Aliphatic Acids, Esters, Alcohols & Derivatives
• Mol File: 108-29-2.mol

Chemical Properties

• Melting Point: −31 °C(lit.)
• Boiling Point: 207-208 °C(lit.)
• Flash Point: 204.8 °F
• Appearance: Clear colorless/Liquid
• Density: 1.05 g/mL at 25 °C(lit.)
• Vapor Density: 3.45 (vs air)
• Vapor Pressure: 0.235mmHg at 25°C
• Refractive Index: n20/D 1.432(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform, Methanol
• Water Solubility: MISCIBLE
• BRN: 80420
• CAS DataBase Reference: gamma-Valerolactone(CAS DataBase Reference)
• NIST Chemistry Reference: gamma-Valerolactone(108-29-2)
• EPA Substance Registry System: gamma-Valerolactone(108-29-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36-36/37/38
• Safety Statements: 39-26-37/39
• WGK Germany: 2
• RTECS: LU3580000
• TSCA: Yes
• Hazardous Substances Data: 108-29-2(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 108-29-2 differently. You can refer to the following data:
1. Colorless liquid. Surface tension 30 dynes/cm (25C), viscosity 2.18 cP (25C), pH (anhydrous): 7. pH (10% solution in distilled water): 4.2. Miscible with water and most organic solvents, resins, waxes, etc.; slightly misciblewith zein, beeswax, petrolatum; immiscible with anhydrous glycerin, glue, casein, arabic gum, and soybean protein. Combustible.
2. γ-Valerolactone has a sweet, herbaceous odor.

Occurrence

Reported found in boiled beef, beef fat, beer, cacao, Swiss cheese, ground and roasted coffee, roasted filberts, milk fat, dried mushroom, peach, roasted peanuts, heated pork fat, black tea and yogurt. Also reported found in peach, strawberry jam, tomato, wheaten bread, Gruyere cheese, heated butter, cooked beef, white wine, red wine, coffee and Bourbon vanilla.

Uses

Different sources of media describe the Uses of 108-29-2 differently. You can refer to the following data:
1. γ-valerolactone?(GVL) can be used as a green solvent: To transform lignocellulose into furfural using a solid acid catalyst, H-mordenite.To synthesize phosphatidylserine.
2. It finds it application as a food additive that is used to improve the taste or odor of a food. It is also used as toiletry fragrances.
3. γ-Valerolactone is a naturally occurring chemical found in fruits and is frequently used as a food additive. It can be converted to liquid alkenes which can be used as transportation fuels. γ-Valerolactone is widely used in dye baths (coupling agent), brake fluids, cutting oils, and as solvent for adhesives, insecticides, and lacquers.

Preparation

By reduction of levulinic acid followed by cyclization.

Synthesis Reference(s)

Journal of the American Chemical Society, 112, p. 1286, 1990 DOI: 10.1021/ja00159a082Tetrahedron Letters, 26, p. 5639, 1985 DOI: 10.1016/S0040-4039(01)80907-2The Journal of Organic Chemistry, 50, p. 3930, 1985 DOI: 10.1021/jo00220a053

General Description

γ-Valerolactone has been identified as one of the volatile flavor constituents in mango and honey.

Reactivity Profile

gamma-Valerolactone is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. gamma-Valerolactone is incompatible with strong oxidizers. . gamma-Valerolactone is incompatible with strong oxidizing agents. gamma-Valerolactone is also incompatible with strong acids, strong bases and strong reducing agents. .

Biochem/physiol Actions

Odor at 1%

Safety Profile

Moderately toxic by ingestion. A skin irritant. Mutation data reported. Combustible liquid when exposed to heat or flame; can react with oxidizing materials. To fight fire, use water, foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Purify the -lactone by repeated fractional distillation [Boorman & Linstead J Chem Soc 577, 580 1933]. IR: max 1790 (CS2), 1775 (CHCl3) cm-1 [Jones et al. Can J Chem 3 7 2007 1959]. The BF3-complex distils at 110-111o/20mm [Reppe et al. Justus Liebigs Ann Chem 596 179 1955]. It is characterized by conversion to -hydroxy-n-valeramide on treatment with NH3, m 51.5-52o (by slow evaporation of a CHCl3 solution). [Beilstein 17 H 235, 17 I 131, 17 II 288, 17 III/IV 4176, 17/9 V 24.]

InChI:InChI=1/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3/t4-/m0/s1

Upstream product

• 626-95-9 1,4-Pentanediol 
• 38802-24-3 4-hydroxyvaleric amide 
• 1617-32-9 (E)-3-pentenoic acid 
• 13532-37-1 4-hydroxyvaleric acid 
• 27126-42-7 ethyl 4-bromopentanoate 
• 18424-77-6 sodium diethyl methylmalonate 
• 64-17-5 ethanol 
• 123-76-2 levulinic acid 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 591-80-0 pent-4-enoic acid 
• 72842-32-1 4,5-dihydro-5-methyl-3-(phenylsulfonyl)-2(3H)-furanone 
• 4630-06-2 6-methylhept-5-en-2-ol 
• 13880-74-5 4-aminopentanoic acid 
• 15384-37-9 D-xylono-1,4-lactone 

Downstream Products

• 70786-82-2 ethyl 4-chloropentanoate 
• 27126-42-7 ethyl 4-bromopentanoate 
• 147792-82-3 4-(3,4-Dimethylphenyl)valeriansaeure 
• 93736-11-9 4-hydroxy-valeric acid-(2-ethyl-2-phenyl-butylamide) 
• 72806-73-6 5-methyl-3-<(E)-phenylmethylidene>dihydrofuran-2(3H)-one 
• 6724-71-6 5-methyl-1-phenylpyrrolidin-2-one 
• 26232-97-3 4-p-tolylpentanoic acid 
• 16433-43-5 4-phenyl-1-pentanoic acid 
• 626-95-9 1,4-Pentanediol 
• 110-15-6 succinic acid 
• 28591-11-9 4-(2,5-Dimethylphenyl)valeriansaeure 
• 74420-31-8 6-(Phenylsulfonyl)-2-hydroxyundecan-5-one 
• 156300-79-7 2-(4'-hydroxy-1'-oxopentyl)-N,N-bis-(methylethyl)benzamide 
• 112197-32-7 α-(diphenylmethylsilyl)-γ-valerolactone 

Relevant articles and documents

Selective hydrogenation of levulinic acid to valeric acid and valeric biofuels by a Pt/HMFI catalyst

We describe one-pot high-yield catalytic pathways for the conversion of levulinic acid (LA) to valeric acid (VA) or valeric acid esters (so-called valeric biofuels) under relatively mild conditions (2 or 8 bar H2, 200 °C). A thorough screening study reveals that a HMFI zeolite-supported Pt metal cluster (Pt/HMFI) with an average cluster size of 1.9 nm shows the highest yield of VA (99%) under solvent-free conditions. The use of ethanol or methanol as solvent changes the selectivity, resulting in 81-84% yields of ethyl valerate (EV) or methyl valerate (MV). Pt/HMFI is also effective for selective formation of valeric acid esters from γVL in alcohols under H2. Kinetics, in situ infrared (IR), and acidity-activity relationship studies show a cooperative mechanism of Pt and Bronsted acid sites of HMFI. VA formation from LA can be driven by Pt-catalyzed hydrogenation of LA to γVL, which undergoes proton-assisted ring-opening by HMFI, followed by Pt-catalyzed hydrogenation. Valeric ester formation from LA is driven by esterification of LA to levulinic ester, which is hydrogenated by Pt. the Partner Organisations 2014.

Maximising opportunities in supercritical chemistry: The continuous conversion of levulinic acid to γ-valerolactone in CO2

Phase behaviour is manipulated during the hydrogenation of aqueous levulinic acid in supercritical CO2 to separate almost pure γ-valerolactone from water and unreacted acid with reduced energy requirements compared to conventional processing. The Royal Society of Chemistry.

Influence of W on the reduction behaviour and Br?nsted acidity of Ni/TiO2catalyst in the hydrogenation of levulinic acid to valeric acid: Pyridine adsorbed DRIFTS study

Effect of W on 20 wt%Ni/TiO2catalyst is examined in the hydrogenation of levulinic acid (LA) to valeric acid at ambient H2pressure. The interaction between W and Ni had a significant influence on the hydrogenation activity and product selectivity. The H2-TPR (temperature programmed reduction) results emphasized a shift in Tmaxto very high temperatures due to W species which are in close proximity to Ni particles. The N2O decomposition measurements showed a decrease in N2O uptake with the increase in ‘W’ loadings due to a high ratio of Ni2+/Ni0species at higher tungsten content. X-ray photoelectron spectra (XPS) demonstrated a shift in binding energy to higher owing to a strong interaction between W and Ni particles by the presence of ionic Ni at the near surface region. The ionic Ni species seems to be involved in the conversion of γ-valerolactone (GVL) to valeric acid (VA). Pyridine adsorbed infrared (IR) spectra revealed an enormous increase in surface Br?nsted acidity originated from tungsten interacted Ni/TiO2are the sites responsible for ring opening of GVL to form VA.

Selective and flexible transformation of biomass-derived platform chemicals by a multifunctional catalytic system

(Figure Presented) A sustainable supply chain: The controlled transformation of the biomassderived platform compounds levulinic acid (LA) and itaconic acid (IA) into the corresponding lactones, diols, or cyclic ethers (see picture) by using a multifunctional molecular catalyst is described.

Enhanced Production of Γ-Valerolactone with an Internal Source of Hydrogen on Ca-Modified TiO2 Supported Ru Catalysts

Calcium-modified titania supported Ru catalysts were synthesized and evaluated for the hydrogenation of levulinic acid with formic acid as an internal hydrogen source and water as a green solvent. A new elegant photoassisted method was developed for the synthesis of uniform-size and evenly distributed Ru particles on the titania surface. Compared with the counterpart catalysts prepared by classical wet impregnation, enhanced levulinic acid conversion and γ-valerolactone yield were obtained and further improved through modification of the support by introduction of calcium into the titania support. This synthesis approach resulted in a change of the surface and bulk properties of the support, namely a decrease in the anatase crystallite size and the formation of a new calcium titanate phase. As a consequence, the properties of the catalysts were modified, and smaller ruthenium particles that had stronger interactions with the support were obtained. This affected the strength of the CO adsorption on the catalyst surface and facilitated the reaction performance. The optimum size of Ru particles that allowed for most efficient levulinic acid conversion was established.

Hydrogenation of biomass-derived compounds containing a carbonyl group over a copper-based nanocatalyst: Insight into the origin and influence of surface oxygen vacancies

New Mn-containing spinel-supported copper nanocatalysts were directly generated via a Cu-Mn-Al layered double hydroxide precursor route and employed in gas-phase hydrogenation of dimethyl succinate (DMS) to γ-butyrolactone (GBL). It was found that the introduction of manganese into catalyst precursors led to the formation of Mn-containing spinel phases, thereby giving rise to highly dispersive Cu0 nanoparticles and a large number of surface defects (i.e., oxygen vacancies (Ov), Mn2+ species) in reduced catalysts. As-formed copper-based nanocatalysts exhibited exceptional catalytic hydrogenation performance with stability enduring up to 100 h. Such high catalytic efficiency could reasonably be attributed to the surface synergism between Mn2+-Ov-Mn2+ defect structures and active metallic copper species, which controlled the key to hydrogenation related to the adsorption of DMS molecules and following activation of carbonyl groups and the dissociation of hydrogen. Most importantly, such copper-based nanocatalysts displayed great potential applications in the hydrogenations of other biomass-derived compounds containing carbonyl groups (e.g., acetol, levulinic acid, levulinic acid esters, and furfural). The present strategy enables us to tune the surface structures of catalysts for designing new type of copper-based catalysts with significantly enhanced catalytic performance.

Sustainable Strategy Utilizing Biomass: Visible-Light-Mediated Synthesis of γ-Valerolactone

A novel sustainable approach to valued γ-valerolactone was investigated. This approach exploits the visible-light-mediated conversion of biomass-derived levulinic acid by using a bimetallic catalyst on a graphitic carbon nitride, AgPd@g-C3N4. Two on one: A novel approach to γ-valerolactone is described that exploits the visible-light-mediated conversion of biomass-derived levulinic acid by using a bimetallic catalyst on graphitic carbon nitride, AgPd@g-C3N4.

A novel hafnium-graphite oxide catalyst for the Meerwein-Ponndorf-Verley reaction and the activation effect of the solvent

Construction and application of novel hydrogenation catalysts is important for the conversion of carbonyl or aldehyde compounds into alcohols in the field of biomass utilization. In this work, a novel, efficient, and easily prepared hafnium-graphite oxide (Hf-GO) catalyst was constructed via the coordination between Hf4+ and the carboxylic groups in GO. The catalyst was applied into the hydrogenation of biomass derived carbonyl compounds via the Meerwein-Ponndorf-Verley (MPV) reaction. The catalyst gave high efficiency under mild conditions. An interesting phenomenon was found whereby the activity of the catalyst increased gradually in the initial stage during reaction. The solvent, isopropanol, was proved to have an activation effect on the catalyst, and the activation effect varied with different alcohols and temperatures. Further characterizations showed that isopropanol played the activation effect via replacing the residual solvent (DMF) in micro- and mesopores during the preparation process, which was hard to be completely removed by common drying process.

Conversion of biomass-derived levulinate and formate esters into γ-valerolactone over supported gold catalysts

The utilization of biomass has recently attracted tremendous attention as a potential alternative to petroleum for the production of liquid fuels and chemicals. We report an efficient alcohol-mediated reactive extraction strategy by which a hydrophobic mixture of butyl levulinate and formate esters, derived from cellulosic biomass, can be converted to valuable γ-valerolactone (GVL) by a simple supported gold catalyst system without need of an external hydrogen source. The essential role of the supported gold is to facilitate the rapid and selective decomposition of butyl formate to produce a hydrogen stream, which enables the highly effective reduction of butyl levulinate into GVL. This protocol simplifies the recovery and recycling of sulfuric acid, which is used for cellulose deconstruction.

Stabilization of cobalt catalysts by embedment for efficient production of valeric biofuel

We herein report, for the first time, a bifunctional base-metal catalyst (Co@HZSM-5) that acts as an efficient alternative to noble-metal catalysts (e.g., Pt, Ru) for the conversion of levulinic acid into valeric biofuel under batch and fixed-bed reactor conditions. The cobalt nanoparticles were embedded in HZSM-5 crystals and catalyzed the sequential hydrogenations of the ketone and alkene functional groups; meanwhile, the acidic zeolite catalyzed the ring opening of the γ-valerolactone intermediate. Although base metals (e.g., Co) are abundant and inexpensive, their sintering and/or leaching under liquid-phase conditions always lead to the irreversible deactivation of the catalyst. In this system, the embedment structure stabilizes the nanoparticles, and Co@HZSM-5 could be used up to eight times. This work provides a practical clue toward the stabilization of base-metal catalysts and will inspire the development of large-scale biorefinery.