在常压和加压条件下直接合成萜烯马来酸二甲酯加合物

Synthesis of Terpene-dimethyl Maleate Adduct under Atmospheric and Pressurized Conditions

摘要: 以工业双戊烯为原料,马来酸二甲酯为双烯加成试剂,在常压和加压两种条件下合成了萜烯马来酸二甲酯加合物。常压下,加热至 185 ℃ 回流 10 h,产率为 55 %;压力反应釜中,压力为 1.5 MPa,反应温度为 240 ℃,反应 2 h 即可进行完全,产率为 78.6 %。纯化产物用GC-MS、1H NMR 和FT-IR进行了表征。GC-MS表明经蒸馏纯化的产物中分子离子峰质荷比为280.1的萜烯马来酸二甲酯同分异构体约有20个,纯度为 95.2 %。经产物的 1H NMR 计算得到产物中Diels-Alder加成物质量分数为 35 %。

Abstract: Terpene-dimethyl maleate adduct was prepared under atmospheric and pressurized conditions from industrial dipentene and dimethyl maleate as a dienophile. Under atmospheric condition, the yield of terpene-dimethyl maleate adduct was 55% after reflux at 185 ℃ for 10 h. In the hermetic autoclave, the yield of terpene-dimethyl maleate adduct achieved at 78.6 % after 2 h at 240 ℃ and 1.5 MPa. The adduct was characterized by GC-MS, 1H NMR and FT-IR. GC-MS indicated that there were 20 geometric isomers. The mass charge ratio of those molecular ion peaks was 280.1 in the purified adduct and the purity was 95.2%. The content of the Diels-Alder adduct was about 35% of the purified adduct which was calculated from 1H NMR.