| Identification | More | [Name]
delta-Valerolactone | [CAS]
542-28-9 | [Synonyms]
4,5-DIHYDRO-5-METHYL-2 (3H)-FURANONE
4-HYDROXYPENTANOIC ACID LACTONE
4-HYDROXYVALERIC ACID G-LACTONE
4-PENTANOLIDE
4-VALEROLACTONE
DELTA-VALEROLACTONE
D-VALEROLACTONE
FEMA 3103
GAMMA-METHYL-GAMMA-BUTYROLACTONE
GAMMA-PENTANOLACTONE
GAMMA-VALEROLACTONE
G-VALEROLACTONE
TETRAHYDRO-2H-2-PYRANONE
TETRAHYDRO-2H-PYRAN-2-ONE
VALEROLACTONE, GAMMA-
1,2-pyrone,tetrahydro-
1-Oxacyclohexan-2-one
2H-pyran-2-one,tetrahydro-
5-Hydroxypentanoic acid delta-lactone
5-pentanolide | [EINECS(EC#)]
203-569-5 | [Molecular Formula]
C5H8O2 | [MDL Number]
MFCD00005400 | [Molecular Weight]
100.12 | [MOL File]
542-28-9.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to pale yellow liquid | [Melting point ]
-13 °C | [Boiling point ]
230 °C | [density ]
1.105 g/mL at 20 °C
| [vapor density ]
3.45 (vs air)
| [vapor pressure ]
8.8Pa at 20℃ | [refractive index ]
n20/D 1.457(lit.)
| [Fp ]
212 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform, Ethyl Acetate, Methanol | [form ]
Liquid | [color ]
Clear colorless to pale yellow | [Water Solubility ]
miscible | [BRN ]
106436 | [Stability:]
Moisture Sensitive | [LogP]
0 at 23℃ | [CAS DataBase Reference]
542-28-9(CAS DataBase Reference) | [NIST Chemistry Reference]
2H-Pyran-2-one, tetrahydro-(542-28-9) | [EPA Substance Registry System]
542-28-9(EPA Substance) |
| Questions And Answer | Back Directory | [Description]
δ-valerolactone, also known as 1,5-valerolactone, delta-valerolactone, tetrahydro-2H-2-pyrone, tetrahydro-o-pyrone, tetrahydrocoumarin; the English name is Delta -Valerolactone, the abbreviated name is generally δ -VL or DVL, and the molecular formula is C5H802. | [Uses]
Due to its good application flexibility, lower biological toxicity, more derivative compounds, easy polymerization and greatly increase the viscosity of coatings and other characteristics, delta-valerolactone is widely used in polyesters, polyurethanes, special solvents, and coatings. | [Preparation]
In the first step, the 1,5-pentanediol raw material is fed into the drying tower for dehydration, to ensure that the water content is less than 1wt%, under optimized conditions, less than 0.5wt%, further optimization, less than 0.1wt%, further optimization situation , Less than 0.05wt%, that is, 500wppm; in the second step, the dried 1,5-pentanediol is mixed with hydrogen and then enters the vaporizer. The molar ratio of hydrogen to 1,5-pentanediol is 10-5:1 The third step will be vaporized 1,5-pentanediol and hydrogen into the dehydrogenation reactor, under the normal pressure of 0.1MPa, 230-270 conditions, under the action of the dehydrogenation catalyst, 1,5-pentanediol Alcohol is converted into δ-valerolactone, in which the yield of δ-valerolactone exceeds 98%, and the water content of the exported crude product is less than 0.5wt%. |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection . | [RIDADR ]
UN1760 | [WGK Germany ]
3
| [RTECS ]
LU3580000
| [Hazard Note ]
Irritant/Keep Cold | [TSCA ]
Yes | [HazardClass ]
8 | [HS Code ]
29322090 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to pale yellow liquid | [Definition]
ChEBI: The simplest member of the class of delta-lactone that is tetrahydro-2H-pyran substituted by an oxo group at position 2. | [Synthesis Reference(s)]
Canadian Journal of Chemistry, 52, p. 3651, 1974 DOI: 10.1139/v74-546
The Journal of Organic Chemistry, 48, p. 5160, 1983 DOI: 10.1021/jo00174a003
Journal of the American Chemical Society, 69, p. 1545, 1947 DOI: 10.1021/ja01198a517 | [Flammability and Explosibility]
Nonflammable | [Purification Methods]
Purify the -lactone by repeated fractional distillation. IR: max 1750 (in CS2), 1732 (in CHCl3),1748 (in CCl4) and 1733 (in MeOH) cm-1 [Huisgen & Ott Tetrahedron 6 253 1959, Linstead & Rydon J Chem Soc 580 1933, Jones et al. Can J Chem 37 2007 1959]. [Beilstein 17 H 235, 17 II 287, 17 III/IV 4169,17/9 V 17.] | [References]
[1] BREI V, VARVARIN A, PRUDIUS S. One-pot synthesis of δ-valerolactone from tetrahydrofurfuryl alcohol and δ-valerolactone amidation over Сu/ZnO-Al2O3 catalyst[C]. 2016: 0. DOI:10.15407/HFTP07.04.395.
[2] ROBSON F. STOREY Douglas C H. Copolymerization of ϵ-caprolactone and δ-valerolactone[J]. Macromolecular Symposia, 1991, 42-43 1: 185-193. DOI:10.1002/masy.19910420115.
[3] YA. V. SOLOVYOVA. Synthesis of δ-Valerolactone Using Stable Hydrogen Peroxide Derivatives[J]. Russian Journal of Organic Chemistry, 2022, 58 4: 480-483. DOI:10.1134/S1070428022040029.
[4] LIN Y, CHEN K, BAI T, et al. Carbenium-Based Cationic Ring-Opening Polymerization of CO2-Based Disubstituted δ-Valerolactone[J]. ACS Macro Letters, 2025, 86 1. DOI:10.1021/acsmacrolett.5c00005.
[5] PHORNWALAN NANTHANANON Yong K K. Effect of chain architecture and comonomer ratio on the biodegradability and thermal stability of biodegradable copolymers of l-lactide and δ-valerolactone†[J]. Green Chemistry, 2024, 26 4: Pages 2031-2043. DOI:10.1039/d3gc04140a.
[6] MASAHIRO YAMASHITA. Organolanthanide-Initiated Living Polymerizations of ε-Caprolactone, δ-Valerolactone, and β-Propiolactone[J]. Macromolecules, 1996, 29 5: 1798-1806. DOI:10.1021/ma951400n.
[7] K. N. HOUK. Why δ-Valerolactone Polymerizes and γ-Butyrolactone Does Not[J]. The Journal of Organic Chemistry, 2008, 73 7: 2674-2678. DOI:10.1021/jo702567v. |
|
|