Sulfuric Acid → Gamma-Decalactone

Participants

Reaction Steps

The circulation type electrolytic apparatus as described in Example 24 and 10 wt% sulfuric acid as an anolyte were used. As a catholyte was used a mixture of 73.9 g (0.648 mol) of heptanal, 18.6 g (0.216 mol) of methyl acrylate, 418 g of water, 53 g (0.149 mol) of tetraethylammonium sulfate and 36 g (0.062 mol) of tetra-n-butylammonium sulfate. The electrolysis was carried out at a catholyte temperature of 27° to 29° C. and a current density of 10.0 A/dm2 while stirring the catholyte in the electrolytic apparatus by circulating the catholyte at a flow rate of 200 cm/sec between the cathode chamber and the catholyte tank. A mixture of 45.9 g (0.403 mol) of heptanal and 48.8 g (0.567 mol) of methyl acrylate was fed into the catholyte tank little by little over five hours during the electrolysis. When the relative current quantity reached 66%, the electrolysis was stopped. During the electrolysis, the voltage fluctuated between 5.8 V and 5.9 V. After the electrolysis, the catholyte was allowed to stand so as to be separated into an organic phase and a water phase. The organic phase was washed with 50 g of water and, then, distilled. 10 g of methyl acrylate was recovered from the organic and water phases. 66 g of heptanal was recovered from the organic phase. By distilling the organic phase, 22 g of dimethyl adipate as a by-product and 57 g of 4-n-hexyl-4-butanolide were obtained. The results are summarized as follows:

Provenance & Evidence