Study on the Hydration of α-Pinene Catalyzed by α-Hydroxycarboxylic Acid–Boric Acid Composite Catalysts

In this study, seven types of α-hydroxycarboxylic acids were selected to form composite catalysts with boric acid, and their catalytic properties were studied using the catalytic hydration of α-pinene. The results showed that the composite catalyst of boric acid and tartaric acid had the highest cat...

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Main Authors: Zhonglei Meng, Rongxiu Qin, Rusi Wen, Guiqing Li, Zhongyun Liang, Junkang Xie, Zhangqi Yang, Yonghong Zhou
Format: Article
Language:English
Published: MDPI AG 2023-04-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/28/7/3202
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author Zhonglei Meng
Rongxiu Qin
Rusi Wen
Guiqing Li
Zhongyun Liang
Junkang Xie
Zhangqi Yang
Yonghong Zhou
author_facet Zhonglei Meng
Rongxiu Qin
Rusi Wen
Guiqing Li
Zhongyun Liang
Junkang Xie
Zhangqi Yang
Yonghong Zhou
author_sort Zhonglei Meng
collection DOAJ
description In this study, seven types of α-hydroxycarboxylic acids were selected to form composite catalysts with boric acid, and their catalytic properties were studied using the catalytic hydration of α-pinene. The results showed that the composite catalyst of boric acid and tartaric acid had the highest catalytic activity. With an α-pinene, water, acetic acid, tartaric acid, and boric acid mass ratio of 10:10:25:0.5:0.4, the reaction temperature was 60 °C, the reaction time was 24 h, the conversion of α-pinene was 96.1%, and the selectivity of terpineol was 58.7%. The composite catalyst composed of boric acid and mandelic acid directly catalyzed the hydration of α-pinene in the absence of a solvent. Under the optimal conditions, the conversion of α-pinene reached 96.1%, and the selectivity of terpineol was 55.5%. When the composite catalyst catalyzed α-pinene to synthesize terpineol in one step, the terpineol was optically active, and terpineol synthesized using the two-step method with the dehydration of <i>p</i>-menthane-1,8-diol monohydrate was racemic. These composite catalysts may offer good application prospects in the synthesis of terpineol.
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spelling doaj.art-7eae063e85154a96936d60e3b7f2548b2023-11-17T17:15:02ZengMDPI AGMolecules1420-30492023-04-01287320210.3390/molecules28073202Study on the Hydration of α-Pinene Catalyzed by α-Hydroxycarboxylic Acid–Boric Acid Composite CatalystsZhonglei Meng0Rongxiu Qin1Rusi Wen2Guiqing Li3Zhongyun Liang4Junkang Xie5Zhangqi Yang6Yonghong Zhou7Guangxi Key Laboratory of Superior Timber Trees Resource Cultivation, Guangxi Forestry Research Institute, Nanning 530002, ChinaGuangxi Key Laboratory of Superior Timber Trees Resource Cultivation, Guangxi Forestry Research Institute, Nanning 530002, ChinaGuangxi Key Laboratory of Superior Timber Trees Resource Cultivation, Guangxi Forestry Research Institute, Nanning 530002, ChinaGuangxi Key Laboratory of Superior Timber Trees Resource Cultivation, Guangxi Forestry Research Institute, Nanning 530002, ChinaGuangxi Key Laboratory of Superior Timber Trees Resource Cultivation, Guangxi Forestry Research Institute, Nanning 530002, ChinaGuangxi Key Laboratory of Superior Timber Trees Resource Cultivation, Guangxi Forestry Research Institute, Nanning 530002, ChinaGuangxi Key Laboratory of Superior Timber Trees Resource Cultivation, Guangxi Forestry Research Institute, Nanning 530002, ChinaInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry (CAF), Nanjing 210042, ChinaIn this study, seven types of α-hydroxycarboxylic acids were selected to form composite catalysts with boric acid, and their catalytic properties were studied using the catalytic hydration of α-pinene. The results showed that the composite catalyst of boric acid and tartaric acid had the highest catalytic activity. With an α-pinene, water, acetic acid, tartaric acid, and boric acid mass ratio of 10:10:25:0.5:0.4, the reaction temperature was 60 °C, the reaction time was 24 h, the conversion of α-pinene was 96.1%, and the selectivity of terpineol was 58.7%. The composite catalyst composed of boric acid and mandelic acid directly catalyzed the hydration of α-pinene in the absence of a solvent. Under the optimal conditions, the conversion of α-pinene reached 96.1%, and the selectivity of terpineol was 55.5%. When the composite catalyst catalyzed α-pinene to synthesize terpineol in one step, the terpineol was optically active, and terpineol synthesized using the two-step method with the dehydration of <i>p</i>-menthane-1,8-diol monohydrate was racemic. These composite catalysts may offer good application prospects in the synthesis of terpineol.https://www.mdpi.com/1420-3049/28/7/3202α-hydroxycarboxylic acid–boric acid complexesgreen catalysthydration of α-pinenesolvent-freeterpineol<i>p</i>-menthane-1,8-diol monohydrate
spellingShingle Zhonglei Meng
Rongxiu Qin
Rusi Wen
Guiqing Li
Zhongyun Liang
Junkang Xie
Zhangqi Yang
Yonghong Zhou
Study on the Hydration of α-Pinene Catalyzed by α-Hydroxycarboxylic Acid–Boric Acid Composite Catalysts
Molecules
α-hydroxycarboxylic acid–boric acid complexes
green catalyst
hydration of α-pinene
solvent-free
terpineol
<i>p</i>-menthane-1,8-diol monohydrate
title Study on the Hydration of α-Pinene Catalyzed by α-Hydroxycarboxylic Acid–Boric Acid Composite Catalysts
title_full Study on the Hydration of α-Pinene Catalyzed by α-Hydroxycarboxylic Acid–Boric Acid Composite Catalysts
title_fullStr Study on the Hydration of α-Pinene Catalyzed by α-Hydroxycarboxylic Acid–Boric Acid Composite Catalysts
title_full_unstemmed Study on the Hydration of α-Pinene Catalyzed by α-Hydroxycarboxylic Acid–Boric Acid Composite Catalysts
title_short Study on the Hydration of α-Pinene Catalyzed by α-Hydroxycarboxylic Acid–Boric Acid Composite Catalysts
title_sort study on the hydration of α pinene catalyzed by α hydroxycarboxylic acid boric acid composite catalysts
topic α-hydroxycarboxylic acid–boric acid complexes
green catalyst
hydration of α-pinene
solvent-free
terpineol
<i>p</i>-menthane-1,8-diol monohydrate
url https://www.mdpi.com/1420-3049/28/7/3202
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