An example of the valorization of terpenes: The selective isomerization of 3-carene to 2-carene in the presence of silica supported nickel catalysts modified by tetrabutyl tin

Pierre Lesage; Jean-Pierre Candy; Christiane Hirigoyen; Francis Humblot; Michel Leconte; Jean Marie Basset

doi:10.1016/1381-1169(96)00126-4

An example of the valorization of terpenes: The selective isomerization of 3-carene to 2-carene in the presence of silica supported nickel catalysts modified by tetrabutyl tin

Pierre Lesage, Jean-Pierre Candy, Christiane Hirigoyen, Francis Humblot, Michel Leconte, Jean Marie Basset^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

The cyclic olefin, 3-carene, undergoes an isomerization of the carbon- carbon double bond to produce 2-carene, a precursor in the synthesis of (-)- menthol. This isomerization is observed over silica supported nickel, but the selectivity is reduced by side reactions producing trimethylheptenes by hydrogenative ring opening of the cyclopropyl ring. Selectivity for C=C bond isomerization is dramatically increased by surface modification of the nickel metal catalyst by reaction with tetra-n-butyl tin. The most selective of these silica supported nickel/tin catalysts produces 2-carene with 91% selectivity at 48% conversion.

Original language	English (US)
Pages (from-to)	303-309
Number of pages	7
Journal	Journal of Molecular Catalysis A: Chemical
Volume	112
Issue number	2
DOIs	https://doi.org/10.1016/1381-1169(96)00126-4
State	Published - Oct 25 1996
Externally published	Yes

Keywords

Carene isomerization
Ni/SiO catalyst
Surface organometallic chemistry
Tetra-n-butyl tin modified catalyst

ASJC Scopus subject areas

Catalysis
Process Chemistry and Technology
Physical and Theoretical Chemistry

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10.1016/1381-1169(96)00126-4

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Lesage, P., Candy, J.-P., Hirigoyen, C., Humblot, F., Leconte, M., & Basset, J. M. (1996). An example of the valorization of terpenes: The selective isomerization of 3-carene to 2-carene in the presence of silica supported nickel catalysts modified by tetrabutyl tin. Journal of Molecular Catalysis A: Chemical, 112(2), 303-309. https://doi.org/10.1016/1381-1169(96)00126-4

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title = "An example of the valorization of terpenes: The selective isomerization of 3-carene to 2-carene in the presence of silica supported nickel catalysts modified by tetrabutyl tin",

abstract = "The cyclic olefin, 3-carene, undergoes an isomerization of the carbon- carbon double bond to produce 2-carene, a precursor in the synthesis of (-)- menthol. This isomerization is observed over silica supported nickel, but the selectivity is reduced by side reactions producing trimethylheptenes by hydrogenative ring opening of the cyclopropyl ring. Selectivity for C=C bond isomerization is dramatically increased by surface modification of the nickel metal catalyst by reaction with tetra-n-butyl tin. The most selective of these silica supported nickel/tin catalysts produces 2-carene with 91% selectivity at 48% conversion.",

keywords = "Carene isomerization, Ni/SiO catalyst, Surface organometallic chemistry, Tetra-n-butyl tin modified catalyst",

author = "Pierre Lesage and Jean-Pierre Candy and Christiane Hirigoyen and Francis Humblot and Michel Leconte and Basset, {Jean Marie}",

year = "1996",

month = oct,

day = "25",

doi = "10.1016/1381-1169(96)00126-4",

language = "English (US)",

volume = "112",

pages = "303--309",

journal = "Journal of Molecular Catalysis A: Chemical",

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publisher = "Elsevier B.V.",

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}

Lesage, P, Candy, J-P, Hirigoyen, C, Humblot, F, Leconte, M & Basset, JM 1996, 'An example of the valorization of terpenes: The selective isomerization of 3-carene to 2-carene in the presence of silica supported nickel catalysts modified by tetrabutyl tin', Journal of Molecular Catalysis A: Chemical, vol. 112, no. 2, pp. 303-309. https://doi.org/10.1016/1381-1169(96)00126-4

An example of the valorization of terpenes: The selective isomerization of 3-carene to 2-carene in the presence of silica supported nickel catalysts modified by tetrabutyl tin. / Lesage, Pierre; Candy, Jean-Pierre; Hirigoyen, Christiane et al.
In: Journal of Molecular Catalysis A: Chemical, Vol. 112, No. 2, 25.10.1996, p. 303-309.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - An example of the valorization of terpenes

T2 - The selective isomerization of 3-carene to 2-carene in the presence of silica supported nickel catalysts modified by tetrabutyl tin

AU - Lesage, Pierre

AU - Candy, Jean-Pierre

AU - Hirigoyen, Christiane

AU - Humblot, Francis

AU - Leconte, Michel

AU - Basset, Jean Marie

PY - 1996/10/25

Y1 - 1996/10/25

N2 - The cyclic olefin, 3-carene, undergoes an isomerization of the carbon- carbon double bond to produce 2-carene, a precursor in the synthesis of (-)- menthol. This isomerization is observed over silica supported nickel, but the selectivity is reduced by side reactions producing trimethylheptenes by hydrogenative ring opening of the cyclopropyl ring. Selectivity for C=C bond isomerization is dramatically increased by surface modification of the nickel metal catalyst by reaction with tetra-n-butyl tin. The most selective of these silica supported nickel/tin catalysts produces 2-carene with 91% selectivity at 48% conversion.

AB - The cyclic olefin, 3-carene, undergoes an isomerization of the carbon- carbon double bond to produce 2-carene, a precursor in the synthesis of (-)- menthol. This isomerization is observed over silica supported nickel, but the selectivity is reduced by side reactions producing trimethylheptenes by hydrogenative ring opening of the cyclopropyl ring. Selectivity for C=C bond isomerization is dramatically increased by surface modification of the nickel metal catalyst by reaction with tetra-n-butyl tin. The most selective of these silica supported nickel/tin catalysts produces 2-carene with 91% selectivity at 48% conversion.

KW - Carene isomerization

KW - Ni/SiO catalyst

KW - Surface organometallic chemistry

KW - Tetra-n-butyl tin modified catalyst

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An example of the valorization of terpenes: The selective isomerization of 3-carene to 2-carene in the presence of silica supported nickel catalysts modified by tetrabutyl tin

Abstract

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ASJC Scopus subject areas

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