67693-94-1

Basic information

• Product Name: 6-ethenyl-3-ethylidenetetrahydro-2H-pyran-2-one
• CAS NO: 67693-94-1
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.1904
• Mol File: 67693-94-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 267.4°C at 760 mmHg
• Flash Point: 106.1°C
• Density: 1.152g/cm³
• Vapor Pressure: 0.00819mmHg at 25°C
• Refractive Index: 1.621
• CAS DataBase Reference: 6-ethenyl-3-ethylidenetetrahydro-2H-pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-ethenyl-3-ethylidenetetrahydro-2H-pyran-2-one(67693-94-1)
• EPA Substance Registry System: 6-ethenyl-3-ethylidenetetrahydro-2H-pyran-2-one(67693-94-1)

Safety Data

• Hazardous Substances Data: 67693-94-1(Hazardous Substances Data)

Upstream product

• 124-38-9 carbon dioxide 
• 106-99-0 buta-1,3-diene 

Downstream Products

• 55191-19-0 dimethyl 2-ethyloctanedioate 

Relevant articles and documents

Synthese von 2-Ethyliden-6-hepten-5-olid

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Copolymerization of carbon dioxide and butadiene via a lactone intermediate

Although carbon dioxide has attracted broad interest as a renewable carbon feedstock, its use as a monomer in copolymerization with olefins has long been an elusive endeavour. A major obstacle for this process is that the propagation step involving carbon dioxide is endothermic; typically, attempted reactions between carbon dioxide and an olefin preferentially yield olefin homopolymerization. Here we report a strategy to circumvent the thermodynamic and kinetic barriers for copolymerizations of carbon dioxide and olefins by using a metastable lactone intermediate, 3-ethylidene-6-vinyltetrahydro-2H- pyran-2-one, which is formed by the palladium-catalysed condensation of carbon dioxide and 1,3-butadiene. Subsequent free-radical polymerization of the lactone intermediate afforded polymers of high molecular weight with a carbon dioxide content of 33 mol% (29 wt%). Furthermore, the protocol was applied successfully to a one-pot copolymerization of carbon dioxide and 1,3-butadiene, and one-pot terpolymerizations of carbon dioxide, butadiene and another 1,3-diene. This copolymerization technique provides access to a new class of polymeric materials made from carbon dioxide.