Selective Oxidative Lactonization of 1,6-Hexanediol into ε-Caprolactone

Xiaoyu Shen; Zhongtian Du; Bairui Guo; Zhongxu Guo; Changhai Liang

doi:10.7536/PC221209

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Prog Chem ›› 2023, Vol. 35 ›› Issue (8) : 1191-1198. DOI: 10.7536/PC221209

Review

Selective Oxidative Lactonization of 1,6-Hexanediol into ε-Caprolactone

Xiaoyu Shen ¹ ,
Zhongtian Du ¹^,^* ,
Bairui Guo ¹ ,
Zhongxu Guo ¹ ,
Changhai Liang ¹^,²^,^*

Author information +

History +

Abstract

ε-Caprolactone is a key monomer for the synthesis of poly(ε-caprolactone) (PCL) with good biocompatibility and biodegradability, and relevant polymer materials could be applied in pharmaceutical, medicinal, and packaging applications. Green and economic synthesis of ε-caprolactone is vital to popularize such eco-friendly polymers, and selective oxidative lactonization of 1,6-hexanediol into ε-caprolactone remains to be developed. In this review, different routes for the synthesis of ε-caprolactone such as Baeyer-Villiger oxidation of cyclohexanone and oxidative lactonization of 1,6-hexanediol are comparatively analyzed. According to whether electron acceptors (oxidants) are added to the reaction systems, the related advances of oxidative lactonization of 1,6-hexanediol are summarized, and the advantages and disadvantages of the corresponding reaction systems and catalysts are reviewed. The development trend of oxidative lactonization of 1,6-hexanediol into ε-caprolactone is also proposed.

Contents

1 Introduction

2 Catalytic oxidation processes

2.1 Carbonyl compounds act as electron acceptors

2.2 Molecular oxygen acts as the electron acceptor

2.3 H₂O₂acts as the oxidant

3 Catalytic dehydrogenation

3.1 Homogeneous catalysts

3.2 Heterogeneous catalysts

4 Conclusion and outlook

Key words

poly(ε-caprolactone) / ε-caprolactone / 1,6-hexanediol / catalytic oxidation / catalytic dehydrogenation / molecular oxygen

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Xiaoyu Shen , Zhongtian Du , Bairui Guo , et al . Selective Oxidative Lactonization of 1,6-Hexanediol into ε-Caprolactone[J]. Progress in Chemistry. 2023, 35(8): 1191-1198 https://doi.org/10.7536/PC221209

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