Ammonium Phosphotungstate Bonded on Imidazolized Activated Carbon for Selective Catalytic Rearrangement of α-Epoxypinane to Carveol

IF 3.8 3区化学 Q2 CHEMISTRY, PHYSICAL

Catalysts Pub Date : 2024-01-03 DOI:10.3390/catal14010036

Min Zheng, Xiangzhou Li, Dulin Yin, Steven R. Kirk, Hui Li, Peng Zhou, Yanhong Yang

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Abstract

Carveol is a rare fine chemical with specific biological activities and functions in nature. The artificial synthesis of carveol from plentiful and cheap turpentine is expected to further improve development of pharmaceutical and industrial applications. A new green catalytic system for the preparation of high-value carveol from α-epoxypinane is presented. A novel ammonium salt solid acid (AC-COIMI-NH4PW) was obtained from phosphotungstic acid bonded with imidazole basic site on nitrogen-doped activated carbon which, after ammonia fumigation, presented an excellent catalytic performance for the selective rearrangement of α-epoxypinane to carveol in DMF as solvent under mild reaction conditions. At 90 °C for 2 h, the conversion of α-epoxypinane could reach 98.9% and the selectivity of carveol was 50.6%. The acidic catalytic sites exhibited superior durability and the catalytic performance can be restored by supplementing the lost catalyst. Based on the investigation of catalytic processes, a parallel catalytic mechanism for the main product was proposed from the rearrangement of α-epoxypinane on AC-COIMI-NH4PW.

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键合在咪唑化活性炭上的磷钨酸铵用于选择性催化 α-环氧辛烷重排为卡维醇

香芹酚是一种稀有的精细化学品，在自然界中具有特殊的生物活性和功能。从丰富而廉价的松节油中人工合成香芹酚有望进一步改善医药和工业应用的发展。本文介绍了一种从α-环氧松节油烷制备高价值香芹醇的新型绿色催化体系。新型铵盐固体酸（AC-COIMI-NH4PW）由磷钨酸与掺氮活性炭上的咪唑碱基键合而成，经氨水熏蒸后，在温和的反应条件下，以 DMF 为溶剂将 α-epoxypinane 选择性重排为香芹醇，具有优异的催化性能。在 90 °C 下反应 2 小时，α-环氧松香烷的转化率可达 98.9%，而对香芹醇的选择性为 50.6%。酸性催化位点表现出卓越的耐久性，通过补充损失的催化剂可以恢复催化性能。根据对催化过程的研究，提出了 AC-COIMI-NH4PW 上 α-epoxypinane 重排过程中主要产物的平行催化机理。

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来源期刊

Catalysts CHEMISTRY, PHYSICAL-

CiteScore

6.80

自引率

7.70%

发文量

1330

审稿时长

3 months

期刊介绍： Catalysts (ISSN 2073-4344) is an international open access journal of catalysts and catalyzed reactions. Catalysts publishes reviews, regular research papers (articles) and short communications. Our aim is to encourage scientists to publish their experimental and theoretical results in as much detail as possible. Therefore, there is no restriction on the length of the papers. The full experimental details must be provided so that the results can be reproduced.