delta-Valerolactone

Base Information

• Chemical Name: delta-Valerolactone
• CAS No.: 542-28-9
• Deprecated CAS: 2425576-33-4
• Molecular Formula: C5H8O2
• Molecular Weight: 100.117
• Hs Code.: 29322090
• European Community (EC) Number: 208-807-1
• NSC Number: 65442,6247
• UNII: 14V1X9149L
• DSSTox Substance ID: DTXSID6044438
• Nikkaji Number: J6.398C
• Wikipedia: Delta-Valerolactone
• Wikidata: Q903610
• Metabolomics Workbench ID: 49850
• ChEMBL ID: CHEMBL452383
• Mol file: 542-28-9.mol

Synonyms:Valericacid, 5-hydroxy-, d-lactone (6CI);1-Oxacyclohexan-2-one;2-Oxotetrahydropyran;5-Hydroxypentanoic acid lactone;5-Hydroxypentanoic acid d-lactone;5-Valerolactone;NSC6247;Pentan-5-olide;Pentanoic acid, 5-hydroxy-, d-lactone;Tetrahydro-2-pyranone;Tetrahydro-2H-pyran-2-one;d-Valerolactone;d-Valeryllactone;

Chemical Property of delta-Valerolactone

Chemical Property:

• Appearance/Colour: clear colorless to pale yellow liquid
• Vapor Pressure: 0.129mmHg at 25°C
• Melting Point: -13 °C
• Refractive Index: n20/D 1.457(lit.)
• Boiling Point: 218 °C at 760 mmHg
• Flash Point: 81 °C
• PSA: 26.30000
• Density: 1.065 g/cm³
• LogP: 0.71350
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate, Methanol
• Water Solubility.: miscible
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 78.1

Purity/Quality:

99% ^*data from raw suppliers

δ-Valerolactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCOC(=O)C1
• 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. δ-Valerolactone is a compound commonly used to synthesize copolyesters by means of lipase-catalyzed ring opening polymerization. δ-Valerolactone (tetrahydro-2H-2-pyranone or δ VL) can be used as a monomer unit in the synthesis of poly(δ-valerolactone)s poly(conjugated ester)s via ring-opening polymerization.It can also be used as a starting material in the synthesis of (+)-guadinomic acid , sodium δ-hydroxyvalerate , methyl δ-hydroxyvalerate , and 5-hydroxyvaleraldehyde.

Technology Process of delta-Valerolactone

There total 224 articles about delta-Valerolactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

cyclopentanone (120-92-3) → 3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) + valeric acid (13392-69-3)

Guidance literature:

With 2,3,4,5,6-pentafluoroperoxybenzoic acid; In dichloromethane; 1,2-dichloro-ethane; at 40 ℃; for 6h;

DOI:10.1016/j.mencom.2018.11.027

Reference yield: 30.0%

tetrahydro-2-(benzyloxy)-2H-pyran (1927-62-4) → 3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) + benzyl bromide (100-39-0) + benzaldehyde (100-52-7) + Benzyl 5-bromovalerate (60343-28-4)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In chloroform; Mechanism; Heating; reaction time 15-30 min, other THP ethers;

DOI:10.1080/00397919608003870

Reference yield:

pent-4-enoic acid allyl ester (75265-78-0) → 3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) + 5-methyl-5H-furan-2-one (591-11-7) + 5-methylenedihydrofuran-2-one (10008-73-8) + pent-4-enoic acid (591-80-0)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N,N,N,N,N-hexamethylphosphoric triamide; benzene-d6; at 140 ℃; for 6h;

upstream raw materials:

glutaric anhydride,

2-(tert-butylperoxy)tetrahydro-2H-pyran

δ-chlorovaleronitrile

5-hydroxypentanal

Downstream raw materials:

1,7-dioxaspiro[5.5]undecane

tetrahydro-2H-2-pyranol

α-methyl-δ-valerolactone

1 ,5-pentanediol

Refernces

• 1、 Bertolini, Valentina,Appiani, Rebecca,Pallavicini, Marco,Bolchi, Cristiano. "Green Oxidation of Ketones to Lactones with Oxone in Water". . p. 15712 - 15716. Retrieved 2021/11/01.
• 2、 Peeters, Elise,Pomalaza, Guillaume,Khalil, Ibrahim,Detaille, Arnaud,Debecker, Damien P.,Douvalis, Alexios P.,Dusselier, Michiel,Sels, Bert F.. "Highly Dispersed Sn-beta Zeolites as Active Catalysts for Baeyer-Villiger Oxidation: The Role of Mobile, in Situ Sn(II)O Species in Solid-State Stannation". . p. 5984 - 5998. Retrieved 2021/05/31.