Improved process for the synthesis of [2,2]-paracyclophane

Long Zhang; Juan Wang; Leng Gao; Yulun Xu; Weimin Gao

doi:10.1117/12.667759

23 January 2006 Improved process for the synthesis of [2,2]-paracyclophane

Long Zhang, Juan Wang, Leng Gao, Yulun Xu, Weimin Gao

Proceedings Volume 6029, ICO20: Materials and Nanostructures; 60291G (2006) https://doi.org/10.1117/12.667759
Event: ICO20:Optical Devices and Instruments, 2005, Changchun, China

Abstract

An improved method for the preparation of [2,2]-paracyclophane, which is the monomer of poly-p-xylene widely used as high quality electrical coating material, by Hoffmann elimination employing p-methyl-benzyl chloride and trimethyl amine as main raw materials was developed. Influence of solvent, reaction time, reaction temperature etal on the yield of paracyclophane was investigated experimentally. Suitable reaction parameters were obtained as follows: n(Alkali) : n(Quaternary ammonium) is 5:1; catalyst: 0.2% cupric salt; with 1,4-dioxane as solvent and 0.2% sodium borohydride as reducer, and N₂ as protection gas; reaction temperature 110°C, reaction time is 30 hr, at the condition, the yield of [2,2]-paracyclophane is 78.6%, its purity is over 99.5%, with melting point 284-285°C. Analysis results by IR and melting temperature measurement etal identify the substance synthesized is [2,2]-paracyclophane. And the materials used is industrially available and better yield was obtained comparing with the values present in the patent literatures.

Citation Download Citation

Long Zhang, Juan Wang, Leng Gao, Yulun Xu, and Weimin Gao "Improved process for the synthesis of [2,2]-paracyclophane", Proc. SPIE 6029, ICO20: Materials and Nanostructures, 60291G (23 January 2006); https://doi.org/10.1117/12.667759

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