16837-24-4

Basic information

• Product Name: ethyl 3-(2,5,5-trimethyl-1,3-dioxan-2-yl)propanoate
• CAS NO: 16837-24-4
• Molecular Formula: C₁₂H₂₂O₄
• Molecular Weight: 230.3007
• Mol File: 16837-24-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 271.2°C at 760 mmHg
• Flash Point: 111.4°C
• Density: 0.976g/cm³
• Vapor Pressure: 0.00656mmHg at 25°C
• Refractive Index: 1.427
• CAS DataBase Reference: ethyl 3-(2,5,5-trimethyl-1,3-dioxan-2-yl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-(2,5,5-trimethyl-1,3-dioxan-2-yl)propanoate(16837-24-4)
• EPA Substance Registry System: ethyl 3-(2,5,5-trimethyl-1,3-dioxan-2-yl)propanoate(16837-24-4)

Safety Data

• Hazardous Substances Data: 16837-24-4(Hazardous Substances Data)

Upstream product

• 539-88-8 4-oxopentanoic acid ethyl ester 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 

Relevant articles and documents

Biobased aliphatic polyesters from a spirocyclic dicarboxylate monomer derived from levulinic acid

Levulinic acid derived from lignocellulose is an important biobased building block. Here, we report on the synthesis and polymerization of a rigid spirocyclic diester monomer to produce polyesters and copolyesters. The monomer was prepared via a one-step acid catalyzed ketalization involving ethyl levulinate and pentaerythritol by employing a straightforward, solvent-free, and readily scalable method which required no chromatographic purification. Still, careful removal of traces of water from the spiro-diester prior to polycondensations proved crucial to avoid side reactions. A preliminary life cycle assessment (LCA) in terms of greenhouse gas (GHG) emissions indicated that the corresponding spiro-diacid tended to be environmentally favourable, producing less CO2 emission than e.g., biobased succinic acid and adipic acid. A series of aliphatic polyesters with reasonably high molecular weights was subsequently prepared in melt and modified melt polycondensations of the spiro-diester with 1,4-butanediol, 1,6-hexanediol, neopentyl glycol and 1,4-cyclohexanedimethanol, respectively. The resulting fully amorphous polyesters showed glass transition temperatures in the range 12-49 °C and thermal stability up to 300 °C. Hot-pressed films of the polyesters based on neopentyl glycol and 1,4-cyclohexanedimethanol were transparent and mechanically strong, and dynamic melt rheology showed stable shear moduli over time to indicate good processability. In addition, the spiro-diester monomer was employed in copolycondensations with diethyl adipate and 1,4-butanediol and demonstrated good reactivity and stability. Hence, the results of the present study indicate that the spiro-diester based on levulinic acid is an effective monomer for the preparation of aliphatic polyesters and other condensation polymers.

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