Isomerization of α-pinene oxide in the presence of methyltrioxorhenium(VII)

Sofia M. Bruno; Martyn Pillinger; Fritz E. Kühn; Isabel S. Gonçalves; Anabela A. Valente

doi:10.1016/j.catcom.2013.02.001

Isomerization of α-pinene oxide in the presence of methyltrioxorhenium(VII)

Sofia M. Bruno, Martyn Pillinger, Fritz E. Kühn, Isabel S. Gonçalves, Anabela A. Valente

Associate Professorship of Molecular Catalysis

University of Aveiro

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

10 Scopus citations

Abstract

The catalytic performance of methyltrioxorhenium(VII) (MTO) has been investigated for the first time in the isomerization of α-pinene oxide (PinOx) into campholenic aldehyde (CPA). The high isomerization activity of MTO is coupled with high selectivity to CPA: CPA yield of up to 87% (100% conversion) was obtained by using α,α,α-trifluorotoluene as solvent at 15 C. Catalyst recycling is possible in a relatively simple fashion by using MTO coupled to an appropriate ionic liquid. The catalytic application of MTO in the isomerization of PinOx versus the integrated epoxidation- isomerization process of the conversion of α-pinene into CPA is discussed.

Original language	English
Pages (from-to)	40-44
Number of pages	5
Journal	Catalysis Communications
Volume	35
DOIs	https://doi.org/10.1016/j.catcom.2013.02.001
State	Published - 5 May 2013

Keywords

α-Pinene oxide
Acid catalysis
Campholenic aldehyde
Isomerization
Keywords
Methyltrioxorhenium

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10.1016/j.catcom.2013.02.001

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title = "Isomerization of α-pinene oxide in the presence of methyltrioxorhenium(VII)",

abstract = "The catalytic performance of methyltrioxorhenium(VII) (MTO) has been investigated for the first time in the isomerization of α-pinene oxide (PinOx) into campholenic aldehyde (CPA). The high isomerization activity of MTO is coupled with high selectivity to CPA: CPA yield of up to 87% (100% conversion) was obtained by using α,α,α-trifluorotoluene as solvent at 15 C. Catalyst recycling is possible in a relatively simple fashion by using MTO coupled to an appropriate ionic liquid. The catalytic application of MTO in the isomerization of PinOx versus the integrated epoxidation- isomerization process of the conversion of α-pinene into CPA is discussed.",

keywords = "α-Pinene oxide, Acid catalysis, Campholenic aldehyde, Isomerization, Keywords, Methyltrioxorhenium",

author = "Bruno, {Sofia M.} and Martyn Pillinger and K{\"u}hn, {Fritz E.} and Gon{\c c}alves, {Isabel S.} and Valente, {Anabela A.}",

year = "2013",

month = may,

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doi = "10.1016/j.catcom.2013.02.001",

language = "English",

volume = "35",

pages = "40--44",

journal = "Catalysis Communications",

issn = "1566-7367",

publisher = "Elsevier B.V.",

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TY - JOUR

T1 - Isomerization of α-pinene oxide in the presence of methyltrioxorhenium(VII)

AU - Bruno, Sofia M.

AU - Pillinger, Martyn

AU - Kühn, Fritz E.

AU - Gonçalves, Isabel S.

AU - Valente, Anabela A.

PY - 2013/5/5

Y1 - 2013/5/5

N2 - The catalytic performance of methyltrioxorhenium(VII) (MTO) has been investigated for the first time in the isomerization of α-pinene oxide (PinOx) into campholenic aldehyde (CPA). The high isomerization activity of MTO is coupled with high selectivity to CPA: CPA yield of up to 87% (100% conversion) was obtained by using α,α,α-trifluorotoluene as solvent at 15 C. Catalyst recycling is possible in a relatively simple fashion by using MTO coupled to an appropriate ionic liquid. The catalytic application of MTO in the isomerization of PinOx versus the integrated epoxidation- isomerization process of the conversion of α-pinene into CPA is discussed.

AB - The catalytic performance of methyltrioxorhenium(VII) (MTO) has been investigated for the first time in the isomerization of α-pinene oxide (PinOx) into campholenic aldehyde (CPA). The high isomerization activity of MTO is coupled with high selectivity to CPA: CPA yield of up to 87% (100% conversion) was obtained by using α,α,α-trifluorotoluene as solvent at 15 C. Catalyst recycling is possible in a relatively simple fashion by using MTO coupled to an appropriate ionic liquid. The catalytic application of MTO in the isomerization of PinOx versus the integrated epoxidation- isomerization process of the conversion of α-pinene into CPA is discussed.

KW - α-Pinene oxide

KW - Acid catalysis

KW - Campholenic aldehyde

KW - Isomerization

KW - Keywords

KW - Methyltrioxorhenium

UR - http://www.scopus.com/inward/record.url?scp=84874446586&partnerID=8YFLogxK

U2 - 10.1016/j.catcom.2013.02.001

DO - 10.1016/j.catcom.2013.02.001

M3 - Article

AN - SCOPUS:84874446586

SN - 1566-7367

VL - 35

SP - 40

EP - 44

JO - Catalysis Communications

JF - Catalysis Communications

ER -

Isomerization of α-pinene oxide in the presence of methyltrioxorhenium(VII)

Abstract

Keywords

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