芳香烴與不飽和烴之反應 乙炔與甲苯之縮合－1, 1-二〔甲苯基〕乙烷之合成

Condensation of Aryl and Unsaturated Hydrocarbons-Synthesis of Ditolylethane

賈魁士(Kuei-Shih Chia) ； 王文濱(Ung-Ping Wang)

《化學》 52年3期 (1963/09) Pp. 111-119

https://doi.org/10.6623/chem.1963017

摘要

甲苯和乙炔可用硫酸汞-濃硫酸觸媒進行縮合反應而得二甲苯基乙烷（ditolylethane簡稱DTE）之黃色油狀透明液體（b.p. 150-156°C/11mm., d_4^(20) 0.9775）。反應溫度10°C以下爲佳，觸媒量較多時反應溫度必須保持較低（0°C以下），而觸媒量較少時反應溫度可稍高，但以不超過30°C爲宜。甲苯對乙炔之分子比須要保持3：1而其中一部份之甲苯用爲溶媒以避免過度之縮合反應。攪拌在實驗操作中，極關重要，可使反應熱容易逸散，同時亦可使觸媒能够均一滲入甲苯之內，在適當操作條件下甲苯變化率可達40-60%，二甲苯基乙烷之產率爲60-76%，產品經元素分析之結果符合於該化合物之分子式。關於硫酸汞-硫酸液對本反應之觸媒作用，著者等提出一個反應機構之推論。

並列摘要

The condensation reaction of toluene with acetylene was investigated. Two moles of toluene and one mole of acetylene were condensed in the presence of mercuric sulfate-sulfuric acid catalyst, giving the yellow transparent oily liquid of ditolylethane (Asymmetric, b.p. 150-156°C/11 mm., d_4^(20) 0.9775). The optimum reaction temperature was found to be below 10°C. When a larger amount of catalyst was used, the reaction temperature should be kept at 0°C or below, and on the contrary the reaction temperature could be raised (not exceeding 30°C) when a smaller amount of catalyst was used. The mole-ratio of toluene to acetylene was found to be 3 to 1 and part of the toluene used took the role of a solvent in order to prevent over condensation. It was also found that stirring had the effect of the quick escape of reaction heat and homogenous dispersion of the toluene layer. The authors have also proposed the assuming condensation mechanism on the HgSO_4-H_2SO_4 catalytic action. The yield of ditolylethane based on the reacted toluene was 60-76% and the conversion of toluene was 40-60%. From the result of element analysis it was confirmed that the oily product was coincident to the molecular formula of ditolylethane.