542-28-9 Usage
Description
Delta-Valerolactone, also known as δ-Valerolactone (DVL) or 1,5-valerolactone, is the simplest member of the class of delta-lactone, which is a tetrahydro-2H-pyran substituted by an oxo group at position 2. It is a clear colorless to pale yellow liquid with the molecular formula C5H8O2. Due to its good application flexibility, lower biological toxicity, more derivative compounds, easy polymerization, and its ability to greatly increase the viscosity of coatings, it is widely used in various industries.
Uses
Used in Chemical Synthesis:
Delta-Valerolactone is used as a monomer unit for the synthesis of poly(δ-valerolactone)s and poly(conjugated ester)s via ring-opening polymerization. It is also used as a starting material in the synthesis of various compounds, such as (+)-guadinomic acid, sodium δ-hydroxyvalerate, methyl δ-hydroxyvalerate, and 5-hydroxyvaleraldehyde.
Used in Coatings and Viscosity Enhancement:
Delta-Valerolactone is used as a viscosity enhancer in coatings, thanks to its ability to greatly increase the viscosity of these materials.
Used in Polyesters and Polyurethanes:
Delta-Valerolactone is used in the production of polyesters and polyurethanes, which are versatile materials with a wide range of applications in various industries.
Used in Special Solvents:
Due to its unique chemical properties, delta-Valerolactone is also used in the formulation of special solvents for specific applications.
Used in Enzymatic Polymerization:
Delta-Valerolactone is a compound commonly used to synthesize copolyesters by means of lipase-catalyzed ring-opening polymerization, which is an environmentally friendly and efficient method for producing biodegradable polymers.
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%.
Synthesis Reference(s)
Canadian Journal of Chemistry, 52, p. 3651, 1974 DOI: 10.1139/v74-546The Journal of Organic Chemistry, 48, p. 5160, 1983 DOI: 10.1021/jo00174a003Journal 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.]
Check Digit Verification of cas no
The CAS Registry Mumber 542-28-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 2 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 542-28:
(5*5)+(4*4)+(3*2)+(2*2)+(1*8)=59
59 % 10 = 9
So 542-28-9 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O2/c6-5-3-1-2-4-7-5/h1-4H2
542-28-9Relevant articles and documents
Acceptorless Dehydrogenative Cross-Coupling of Primary Alcohols Catalyzed by an N-Heterocyclic Carbene-Nitrogen-Phosphine Chelated Ruthenium(II) Complex
Chen, Hua,Cui, Tianhua,Fu, Haiyan,He, Xiaochun,Jiang, Weidong,Li, Ruixiang,Nie, Xufeng,Xu, Jiaqi,Yuan, Maolin,Zhao, Ling,Zheng, Xueli
, (2022/04/07)
The acceptorless dehydrogenative cross-coupling of primary alcohols to form cross-esters with the liberation of H2 gas was enabled using a [RuCl(η6-C6H6)(κ2-CNP)][PF6]Cl complex as the catalyst. This sustainable protocol is applicable to a broad range of primary alcohols, particularly for the sterically demanding ones, featuring good functional group tolerance and high selectivity. The good catalytic performance can be attributed to the nitrogen-phosphine-functionalized N-heterocyclic carbene (CNP) ligand, which adopts a facial coordination mode as well as the facile dissociation of coordinated benzene.
Lipase catalysed oxidations in a sugar-derived natural deep eutectic solvent
Vagnoni, Martina,Samorì, Chiara,Pirini, Daniele,Vasquez De Paz, Maria Katrina,Gidey, Dawit Gebremichael,Galletti, Paola
, (2021/05/06)
Chemoenzymatic oxidations involving the CAL-B/H2O2 system was developed in a sugar derived Natural Deep Eutectic Solvent (NaDES) composed by a mixture of glucose, fructose and sucrose. Good to excellent conversions of substrates like cyclooctene, limonene, oleic acid and stilbene to their corresponding epoxides, cyclohexanone to its corresponding lactone and 2-phenylacetophenone to its corresponding ester, demonstrate the viability of the sugar NaDES as a reaction medium for epoxidation and Baeyer-Villiger oxidation.
Green Oxidation of Ketones to Lactones with Oxone in Water
Bertolini, Valentina,Appiani, Rebecca,Pallavicini, Marco,Bolchi, Cristiano
, p. 15712 - 15716 (2021/11/01)
Cyclic ketones were quickly and quantitatively converted to 5-, 6-, and 7-membered lactones, very important synthons, by treatment with Oxone, a cheap, stable, and nonpollutant oxidizing reagent, in 1 M NaH2PO4/Na2HPO4 water solution (pH 7). Under such simple and green conditions, no hydroxyacid was formed, thus making the adoption of more complex and non-eco-friendly procedures previously developed to avoid lactone hydrolysis unnecessary. With some changes, the method was successfully applied also to water-insoluble ketones such as adamantanone, acetophenone, 2-indanone, and the challenging cycloheptanone.