フタル酸エステル類の熱分解に関する研究 (第7報) : フタル酸ビス (2, 4-ジフェニルブチル) の合成と熱分解反応

概要

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A new thermostable plasticizer which is a series of phthalic acid esters was synthesized from 2, 4-diphenyl-1-butene (DPB), the thermal decomposition products from the polystyrene. 2, 4-Diphenylbutanal (DPBAL) was obtained from DPB with electrophilic addition of chromium (VI) dichloride dioxide. 2, 4-Diphenyl-1-butanol (DPBOL) was synthesized by the reduction with LiAlH4 from DPBAL. Bis (2, 4-diphenylbutyl) phthalate (DPBP) which was the intended ester, was made by the reaction of phthaloyl dichloride and DPBOL in the presence of pyridine. The thermal stability of DPBP was measured with the thermogravimetric analysis (TG) which was compared with the typical phthalic acid ester plasticizers. Consequently, it becomes clear that the thermal stability of DPBP (282°C) was rised definitely compared with di-n-butyl phthalate (141°C). It was suggested that a revelation of the thermal stability of DPBP was attributable to the difficulty forming the six membered transition state for cis elimination reaction.
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