Study on Synthesizing Isobornyl Acetate/Isoborneol from Camphene Using α-Hydroxyl Carboxylic Acid Composite Catalyst

ZhongLei, Meng; Rong-xiu, Qin; Wen, Rusi; Li, Guiqing; Liang, Zhongyun; Xie, Junkang; Zhou, Yonghong; Yang, Zhang-Qi

doi:10.3390/molecules28041875

Cited by 2 publications

(2 citation statements)

References 18 publications

(20 reference statements)

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“…The hydration reaction of α-pinene catalyzed by HCA and boric acid can increase the conversion rate of α-pinene [ 12 ]. In the synthesis of isobornyl acetate and isoborneol catalyzed by HCA and boric acid composite catalysts from camphene, HCA and boric acid show significant synergistic catalytic effects [ 13 ]. Because the composite catalyst composed of HCA and boric acid can be used for both aqueous and non-aqueous reactions, it is beneficial to use it for the methylation reactions of fatty acids.…”

Section: Introductionmentioning

confidence: 99%

Effect of Boric Acid on the Ionization Equilibrium of α-Hydroxy Carboxylic Acids and the Study of Its Applications

et al. 2023

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To investigate the synergistic catalytic effects of boric acid and α-hydroxycarboxylic acids (HCAs), we analyzed and measured the effects of the complexation reactions between boric acid and HCAs on the ionization equilibrium of the HCAs. Eight HCAs, glycolic acid, D-(−)-lactic acid, (R)-(−)-mandelic acid, D-gluconic acid, L-(−)-malic acid, L-(+)-tartaric acid, D-(−)-tartaric acid, and citric acid, were selected to measure the pH changes in aqueous HCA solutions after adding boric acid. The results showed that the pH values of the aqueous HCA solutions gradually decreased with an increase in the boric acid molar ratio, and the acidity coefficients when boric acid formed double-ligand complexes with HCAs were smaller than those of the single-ligand complexes. The more hydroxyl groups the HCA contained, the more types of complexes could be formed, and the greater the rate of change in the pH. The total rates of change in the pH of the HCA solutions were in the following order: citric acid > L-(−)-tartaric acid = D-(−)-tartaric acid > D-gluconic acid > (R)-(−)-mandelic acid > L-(−)-malic acid > D-(−)-lactic acid > glycolic acid. The composite catalyst of boric acid and tartaric acid had a high catalytic activity—the yield of methyl palmitate was 98%. After the reaction, the catalyst and methanol could be separated by standing stratification.

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Section: Introductionmentioning

confidence: 99%

Effect of Boric Acid on the Ionization Equilibrium of α-Hydroxy Carboxylic Acids and the Study of Its Applications

et al. 2023

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“…As a result, citric acid-BA complexes have been used to improve the dimensional and thermal stability of bamboo materials [ 25 ]. Composite catalysts composed of BA and HCA were found to exert a good synergistic catalytic effect during the catalysis of the esterification reaction of camphene and the hydration reaction of pinene [ 26 , 27 ]. In a previous study [ 28 ], we analyzed and measured the effects of complexation reactions between BA and HCAs on the ionization equilibrium of the HCAs.…”

Section: Introductionmentioning

confidence: 99%

Complexation of Boronic Acid with Chiral α-Hydroxycarboxylic Acids and the Ability of the Complexes to Catalyze α-Hydroxycarboxylic Acid Esterification

Meng,

Qin,

Wen

et al. 2023

Molecules

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The complexation of boric acid (BA) with various α-hydroxycarboxylic acids (HCAs) was examined by analyzing the change in the optical rotation after the addition of BA to aqueous HCA solutions, and the catalytic properties of the complexes were examined by catalyzing the esterification of the HCAs. The absolute values of the optical rotation of the HCAs increased with increasing BA-to-HCA molar ratio, and the rate of change of the optical rotation gradually decreased as the BA-to-HCA molar ratio increased, reaching a minimum value at a molar ratio of approximately three. As a catalyst, BA could catalyze the acetylation of hydroxyl groups in addition to the esterification of HCAs. Compared to the conventional synthesis routes of ATBC and ATOC, a synthesis route with BA as the catalyst allowed for a lower frequency of catalyst separation and replacement while providing light-colored products. BA could catalyze the formation of triethyl citrate, and the yield of triethyl citrate reached 93.8%. BA could also catalyze the reaction between malic acid and pinene to produce borneol malate. After saponification of borneol malate, borneol was obtained with a yield of 39%.

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Study on Synthesizing Isobornyl Acetate/Isoborneol from Camphene Using α-Hydroxyl Carboxylic Acid Composite Catalyst

Cited by 2 publications

References 18 publications

Effect of Boric Acid on the Ionization Equilibrium of α-Hydroxy Carboxylic Acids and the Study of Its Applications

Effect of Boric Acid on the Ionization Equilibrium of α-Hydroxy Carboxylic Acids and the Study of Its Applications

Complexation of Boronic Acid with Chiral α-Hydroxycarboxylic Acids and the Ability of the Complexes to Catalyze α-Hydroxycarboxylic Acid Esterification

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