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Transformation of monoterpenes and monoterpenoids using gold-based heterogeneous catalysts

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Abstract

Gold is an attractive metal for using as catalyst because is very inert and resistant to air oxidation compared with other metals; furthermore, when gold is dispersed as nanoparticles onto a support it attains exceptional catalytic properties in organic reactions. Some heterogeneous gold catalysts have activity in the transformations of monoterpenes and monoterpenoids, natural organic compounds extracted from plants whose transformations produce substances with applications in fine chemicals, pharmaceuticals, cosmetics, agriculture, polymers and food industries. This review describes the achievements of some transformations of monoterpenes (α-pinene and limonene) and monoterpenoids (α-pinene epoxide, verbenol epoxide, myrtenol, nopol, perillyl alcohol, geraniol, nerol, carveol, citronellol, isoborneol, borneol, menthol, isopulegol, citronellal, carvone oxime and 2-adamantanol) reported from 2002 to 2018 through oxidation, hydrogenation, isomerization and amination over gold-based heterogeneous catalysts.

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Abbreviations

BET:

Brunauer–Emmett–Teller

C:

Activated carbon

cys:

Cysteine

DMCPHP:

(2R)-2-[(1R)-2,2-dimethylcyclopent-3-en-1-yl]-2-hydroxypropanal

DMMBHD:

(2R,3R)-6,6-dimethyl-4-methylidenebicyclo[3.1.1]heptane-2,3-diol

DP:

Deposition–precipitation method

Ex:

Exfoliated

GNP:

Gold nanoparticles

HT:

Hydrotalcite

HTMCPE:

2-Hydroxy-1-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]ethanone

IM:

Impregnation method

M:

Metal

MCM:

Mobil composition of matter silica

met:

Methionine

MeCN:

Acetonitrile

MPCHD:

(1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol

MSU:

Michigan State University silica

n.r.:

Not reported

np:

Nanoparticles

P:

Post-synthesis method

P :

Pressure

PM:

Physical mixing

PVA:

Polyvinyl alcohol

rac:

Prepared with racemic amino acids ligands

SBA:

Santa Barbara amorphous silica

S products :

Products selectivity

T :

Temperature

t :

Time

TBHP:

Tert-butyl hydroperoxide

TEM:

Transmission electron microscopy

TOS:

Time-on-stream

UHP:

Urea hydrogen peroxide

WGSV:

Wet gas space velocity

X substrate :

Substrate conversion

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Acknowledgments

JAB and ALV acknowledge financial support from the Universidad de Antioquia and OFA acknowledges the Universidad Cooperativa de Colombia.

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Authors and Affiliations

  1. Environmental Catalysis Research Group, Chemical Engineering Department, Engineering Faculty, Universidad de Antioquia UdeA, Calle 70 No. 52-21, Medellín, Colombia

    Jaime-Andrés Becerra & Aída-Luz Villa

  2. TERMOMEC, Facultad de Ingeniería, Universidad Cooperativa de Colombia, Calle 50 No. 40-74, Bloque A, Piso 4, Medellín, Colombia

    Óscar Felipe Arbeláez

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  1. Jaime-Andrés Becerra
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  2. Óscar Felipe Arbeláez
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  3. Aída-Luz Villa
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JAB, ALV and OFA wrote manuscript and chose references, contributed to the discussions. JAB edited the figures and references. All authors read and approved the final manuscript version to be submitted.

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Correspondence to Aída-Luz Villa.

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Becerra, JA., Arbeláez, Ó.F. & Villa, AL. Transformation of monoterpenes and monoterpenoids using gold-based heterogeneous catalysts. Braz. J. Chem. Eng. 37, 1–27 (2020). https://doi.org/10.1007/s43153-020-00013-1

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