4-Vinyl-1,3-dioxolan-2-one

Chemical Properties

Colorless liquid

Uses

It is used to synthesize functional polymers.

Uses

4-Vinyl-1,3-dioxolan-2-one may be used in the preparation of 2-arylbenzo[d]thiazole scaffolds.
It may be used in the synthesis of the following multi-functional cyclic carbonates:

• 4,4′-((hexane-1,6-diylbis(sulfanediyl))bis-(ethane-2,1-diyl))bis(1,3-dioxolan-2-one) (Bis-CC)
• 2-ethyl-2-(((3-((2-(2-oxo-1,3-dioxolan-4-yl)-ethyl)thio)propanoyl)oxy) methyl)propane-1,3-diyl bis(3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)thio)propanoate) (Tris-CC)
• 2,2-bis(((3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)-thio)propanoyl)oxy) methyl)propane-1,3-diyl bis(3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)thio)propanoate) (Tetra-CC)

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 2955, 1947 DOI: 10.1021/ja01204a008

General Description

4-Vinyl-1,3-dioxolan-2-one (VEC) is a cyclic carbonate, that can be synthesized from acrolein by reacting with sulfur ylide and CO₂. The ruthenium-catalyzed transfer hydrogenation (TH) of VEC in the presence of 2-propanol forms 1,2-butanediol. Indolines and indoles undergo selective C-H allylation with VEC in the presence of rhodium(III) catalyst.

Synthesis

In a 500 mL four-necked flask, 101.2 g of vinyl monochlorocarbonate, 0.60 g of polymerization inhibitor, 158.3 g of dimethyl carbonate were added, the temperature was raised to 55C, 104.4 g of triethylamine was added dropwise with stirring, and the temperature of the dropwise process was controlled to be 55-65C. The reaction solution was gradually blackened during the reaction. The reaction solution gradually turned black during the reaction. The reaction process was protected by nitrogen. Reaction 15 ~ 16 h, the end of the reaction, while hot filtration, with 158.3 g of dimethyl carbonate to wash the slag three times, add 0.5 g of polymerization inhibitor. Distill at atmospheric pressure at a temperature of not more than 95 , remove the remaining triethylamine and dimethyl carbonate. The product was distilled by rotary evaporator (vacuum 0.003 MPa) at a temperature of not more than 80 , and 34.76 g of vinylidene carbonate was obtained with a yield of 65%. The content of vinylidene carbonate was analyzed by gas chromatography 98.5%.