One-pot synthesis of campholenic aldehyde from α-pinene over Ti-HMS catalyst II: effects of reaction conditions

Suh, Young-Woong; Kim, Nam Kyung; Ahn, Wha Seung; Rhee, Hyun‐Ku

doi:10.1016/s1381-1169(02)00733-1

Cited by 36 publications

(9 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is generally accepted that the formation of 2 is favored in the presence of Lewis acids, whereas Brønsted acids tend to produce a mixture of compounds in low yields, such as trans-carveol (3), trans-sobrerol (4 a), and p-cymene. [6,[8][9][10] Various solid Lewis acids have been used as catalysts for the isomerization of a-pinene oxide into aldehyde 2; [6,8,[10][11][12][13][14] however, most of these reactions are time-consuming and/or involve high catalyst/substrate ratios.…”

Section: Introductionmentioning

confidence: 99%

Phosphotungstic Acid as a Versatile Catalyst for the Synthesis of Fragrance Compounds by α‐Pinene Oxide Isomerization: Solvent‐Induced Chemoselectivity

Rocha

Hoehne

Gusevskaya

2008

Chemistry A European J

View full text Add to dashboard Cite

The remarkable effect of the solvent on the catalytic performance of H3PW12O40, the strongest heteropoly acid in the Keggin series, allows direction of the transformations of alpha-pinene oxide (1) to either campholenic aldehyde (2), trans-carveol (3), trans-sobrerol (4 a), or pinol (5). Each of these expensive fragrance compounds was obtained in good to excellent yields by using an appropriate solvent. Solvent polarity and basicity strongly affect the reaction pathways: nonpolar nonbasic solvents favor the formation of aldehyde 2; polar basic solvents favor the formation of alcohol 3; whereas in polar weakly basic solvents, the major products are compounds 4 a and 5. On the other hand, in 1,4-dioxane, which is a nonpolar basic solvent, both aldehyde 2 and alcohol 3 are formed in comparable amounts. The use of very low catalyst loading (0.005-1 mol %) and the possibility of catalyst recovery and recycling without neutralization are significant advantages of this simple, environmentally benign, and low-cost method. This method represents the first example of the synthesis of isomers from alpha-pinene oxide, other than campholenic aldehyde, with a selectivity that is sufficient for practical usage.

show abstract

Section: Introductionmentioning

confidence: 99%

Phosphotungstic Acid as a Versatile Catalyst for the Synthesis of Fragrance Compounds by α‐Pinene Oxide Isomerization: Solvent‐Induced Chemoselectivity

Rocha

Hoehne

Gusevskaya

2008

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…15,26 These radicals decrease the selectivity for the epoxides by the oxidation reaction. 42 To avoid this problem, attempts were made to directly epoxidize 1,2-limonene oxide to determine if Ti-SBA-16 could also allow producing limonene dioxide. The results are summarized Table 2.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Catalyst-Free Epoxidation of Limonene to Limonene Dioxide

Charbonneau

Foster

Zhao

et al. 2018

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

Limonene dioxide is a platform molecule for the production of new biopolymers. First attempts at limonene epoxidation were made by using low-coordination titanium supported on SBA-16 as the catalyst using tert-butyl hydroperoxide as the oxidizing agent, but no limonene dioxide was obtained. When limonene was substituted by 1,2-limonene oxide, the yield of limonene dioxide was only 13% in the same conditions. Two other techniques, both using in situ generated dimethyl dioxirane by the reaction of acetone with Oxone, have been studied and compared. These reactions are carried out in semibatch conditions and at room temperature. The first double epoxidation of limonene was performed in a conventional biphasic organic−water system and the other in excess acetone. The former epoxidation of limonene using ethyl acetate as the organic phase allowed reaching 95% conversion and yielding 33% of limonene dioxide. In comparison, when the reaction was performed in acetone, a limonene dioxide yield of 97% was observed under optimized conditions. The double epoxidation of limonene should be carried out at room temperature with a flowrate of 4 mL min −1 of aqueous Oxone for a period of 45 min with a stoichiometric excess of 30% of Oxone.

show abstract

“…The α-pinene, a monoterpene hydrocarbon, possesses antimalarial activity [25]. It is used as an important substance in the manufacture of a variety of synthetic aroma chemicals and its epoxide is isomerised to produce campholenic aldehyde, which is an intermediate for the sandalwood fragrance, santalol [26]. [18,19,21,22].…”

Section: Resultsmentioning

confidence: 99%

Characterization of the Essential Oil Composition of Isodon rugosus (Wall. ex Benth.) Codd. from Garhwal region of Western Himalaya

2015

Med Aromat Plants

View full text Add to dashboard Cite

One-pot synthesis of campholenic aldehyde from α-pinene over Ti-HMS catalyst II: effects of reaction conditions

Cited by 36 publications

References 27 publications

Phosphotungstic Acid as a Versatile Catalyst for the Synthesis of Fragrance Compounds by α‐Pinene Oxide Isomerization: Solvent‐Induced Chemoselectivity

Phosphotungstic Acid as a Versatile Catalyst for the Synthesis of Fragrance Compounds by α‐Pinene Oxide Isomerization: Solvent‐Induced Chemoselectivity

Catalyst-Free Epoxidation of Limonene to Limonene Dioxide

Characterization of the Essential Oil Composition of Isodon rugosus (Wall. ex Benth.) Codd. from Garhwal region of Western Himalaya

Contact Info

Product

Resources

About