Synthesis of Biorenewable Terpene Monomers Using Enzymatic Epoxidation under Heterogeneous Batch and Continuous Flow Conditions,ACS Sustainable Chemistry & Engineering

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Synthesis of Biorenewable Terpene Monomers Using Enzymatic Epoxidation under Heterogeneous Batch and Continuous Flow Conditions
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2023-03-16 , DOI: 10.1021/acssuschemeng.3c00370
Arianna Brandolese ₁ , David H Lamparelli ₁ , Miquel A Pericàs _{1,

2} , Arjan W Kleij _{1,

3}

Affiliation

A commercially available Lipase B from Candida antarctica immobilized onto a macroporous support (Novozym 435) has been employed in the presence of H₂O₂ as a benign oxidant for the epoxidation of various biorenewable terpenes. This epoxidation protocol was explored under both heterogeneous batch and continuous flow conditions. The catalyst recyclability was also investigated demonstrating good activity throughout 10 cycles under batch conditions, while the same catalyst system could also be productively used under continuous flow operation for more than 30 h. This practical and relatively safe sustainable flow epoxidation of di- and trisubstituted alkenes by H₂O₂ allows for the production of gram quantities of a range of terpene epoxides. As a proof of principle, the same protocol can also be applied to the epoxidation of biobased polymers as a means to post-functionalize these macromolecules and equip them with cross-linkable epoxy groups.

中文翻译：

非均相间歇和连续流动条件下酶促环氧化合成生物可再生萜烯单体

来自南极假丝酵母的市售脂肪酶 B固定在大孔载体 (Novozym 435) 上，已在 H ₂ O ₂存在下用作良性氧化剂，用于各种生物可再生萜烯的环氧化。在非均相间歇和连续流动条件下探索了该环氧化方案。还研究了催化剂的可回收性，证明在间歇条件下的 10 个循环中具有良好的活性，而相同的催化剂体系也可以在连续流动操作下有效使用超过 30 小时。这种实用且相对安全的可持续流动环氧化二取代和三取代烯烃通过H ₂ O ₂可以生产克量的一系列萜烯环氧化物。作为原理证明，相同的方案也可以应用于生物基聚合物的环氧化，作为对这些大分子进行后官能化并为它们配备可交联环氧基团的手段。

更新日期：2023-03-16

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