Investigating the effect of α-pinene on the ROMP of δ-pinene,Polymer Chemistry

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Investigating the effect of α-pinene on the ROMP of δ-pinene
Polymer Chemistry ( IF 4.1 ) Pub Date : 2021-08-23 , DOI: 10.1039/d1py00931a
Mark R. Yarolimek ₁ , Brianna M. Coia ₁ , Heather R. Bookbinder ₁ , Justin G. Kennemur ₁

Affiliation

Poly(δ-pinene), PδP, is a promising new material derived from naturally abundant α-pinene. One of the persistent by-products in the synthesis of δ-pinene is α-pinene which required intensive and non-sustainable isocyanate chemistry to fully remove. This work presents an in-depth study on the effects that varying quantities of α-pinene has on the ring opening metathesis polymerization (ROMP) of δ-pinene using Grubbs 3^rd generation catalyst (G3). It is determined that G3 is tolerant of low quantities of α-pinene (∼40 equivalents) in the reaction mixture and results in high conversions of δ-pinene and well controlled ROMP. Increasingly higher quantities of α-pinene have an inhibitory effect on conversion and loss of control. ¹H NMR experiments revealed complex signals within the Ru-alkylidene and, surprisingly, the ruthenacyclobutane regions of the spectrum as a result of δ-pinene oligomerization. However, no identifiable signals were produced or lost upon interaction with α-pinene suggesting it does not inhibit ROMP through a productive metathesis event.

中文翻译：

研究α-蒎烯对δ-蒎烯的ROMP的影响

聚（δ-蒎烯），PδP，是一种从天然丰富的α-蒎烯衍生而来的有前途的新材料。δ-蒎烯合成过程中的一种持久性副产物是 α-蒎烯，它需要密集且不可持续的异氰酸酯化学反应才能完全去除。这项工作深入研究了不同数量的 α-蒎烯对使用 Grubbs^第三代催化剂 (G3)的 δ-蒎烯开环复分解聚合 (ROMP) 的影响。确定 G3 可以耐受反应混合物中少量的 α-蒎烯（~40 当量），并导致 δ-蒎烯的高转化率和良好控制的 ROMP。越来越多的α-蒎烯对转化和失控具有抑制作用。¹1 H NMR 实验揭示了 Ru-亚烷基内的复杂信号，令人惊讶的是，由于 δ-蒎烯低聚，在光谱的钌环丁烷区域中出现了复杂的信号。然而，与 α-蒎烯相互作用时没有产生或丢失可识别的信号，表明它不会通过生产性复分解事件抑制 ROMP。

更新日期：2021-08-23

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