Isomerization of linoleic acid over supported metal catalysts

Andreas Bernas; Narendra Kumar; Päivi Mäki-Arvela; Natalya V. Kul'kova; Bjarne Holmbom; Tapio Salmi; Dmitry Yu Murzin

doi:10.1016/S0926-860X(02)00646-4

Isomerization of linoleic acid over supported metal catalysts

Andreas Bernas, Narendra Kumar, Päivi Mäki-Arvela, Natalya V. Kul'kova, Bjarne Holmbom, Tapio Salmi, Dmitry Yu Murzin^*

^*Corresponding author for this work

Laboratory of Industrial Chemistry and Reaction Engineering

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

76 Citations (Scopus)

Abstract

Heterogeneous supported metal catalysts were applied for the isomerization reaction of linoleic acid (cis-9,cis-12-octadecadienoic acid) to conjugated linoleic acid (CLA) between 80 and 120°C in a diluted system. Ru, Ni, Pd, Pt, Rh, Ir, Os, and bimetallic Pt-Rh supported by activated carbon, Al₂O₃, SiO₂Al₂O₃, MCM-22, H-MCM-41, H-Y, and H-β were screened. Catalyst characterization was done by XRD, X-ray fluorescence, XPS, H₂-TPD, DCP-AES, and nitrogen adsorption techniques. The isomerization reaction was conducted batchwise in both 1-octanol and n-decane as solvents. Reactions taking place were the isomerization of linoleic acid to CLA, hydrogenation of linoleic acid and CLA to monounsaturated octadecenoic acids (oleic acid, elaidic acid, cis-vaccenic acid, and trans-vaccenic acid), as well as the further hydrogenation of monounsaturated acids to stearic acid (n-octadecanoic acid) with isomerization and hydrogenation being two competing parallel reactions. The isomerization reaction was enhanced by catalyst preactivation under hydrogen. The presence of chemisorbed hydrogen increased the conversion but reduced the isomerization selectivity. Ru and Ni showed the best isomerization properties whereas Pd favored the double bond hydrogenation reaction.

Original language	English
Pages (from-to)	257-275
Number of pages	19
Journal	Applied Catalysis A: General
Volume	245
Issue number	2
DOIs	https://doi.org/10.1016/S0926-860X(02)00646-4
Publication status	Published - 10 Jun 2003
MoE publication type	A1 Journal article-refereed

Funding

This work is part of the activities at the Åbo Akademi Process Chemistry Group within the Finnish Centre of Excellence Programme (2000–2005) by the Academy of Finland. Financial support from the Raisio Group Research Foundation is gratefully acknowledged. The authors express their gratitude to Markku Reunanen for his contribution to the GC–MS analyses.

Keywords

Conjugated linoleic acid (CLA)
Double bond migration
Functional food
Hydrogenation
Isomerization
Linoleic acid
Supported metal catalysts

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10.1016/S0926-860X(02)00646-4

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title = "Isomerization of linoleic acid over supported metal catalysts",

abstract = "Heterogeneous supported metal catalysts were applied for the isomerization reaction of linoleic acid (cis-9,cis-12-octadecadienoic acid) to conjugated linoleic acid (CLA) between 80 and 120°C in a diluted system. Ru, Ni, Pd, Pt, Rh, Ir, Os, and bimetallic Pt-Rh supported by activated carbon, Al2O3, SiO2Al2O3, MCM-22, H-MCM-41, H-Y, and H-β were screened. Catalyst characterization was done by XRD, X-ray fluorescence, XPS, H2-TPD, DCP-AES, and nitrogen adsorption techniques. The isomerization reaction was conducted batchwise in both 1-octanol and n-decane as solvents. Reactions taking place were the isomerization of linoleic acid to CLA, hydrogenation of linoleic acid and CLA to monounsaturated octadecenoic acids (oleic acid, elaidic acid, cis-vaccenic acid, and trans-vaccenic acid), as well as the further hydrogenation of monounsaturated acids to stearic acid (n-octadecanoic acid) with isomerization and hydrogenation being two competing parallel reactions. The isomerization reaction was enhanced by catalyst preactivation under hydrogen. The presence of chemisorbed hydrogen increased the conversion but reduced the isomerization selectivity. Ru and Ni showed the best isomerization properties whereas Pd favored the double bond hydrogenation reaction.",

keywords = "Conjugated linoleic acid (CLA), Double bond migration, Functional food, Hydrogenation, Isomerization, Linoleic acid, Supported metal catalysts",

author = "Andreas Bernas and Narendra Kumar and P{\"a}ivi M{\"a}ki-Arvela and Kul'kova, \{Natalya V.\} and Bjarne Holmbom and Tapio Salmi and Murzin, \{Dmitry Yu\}",

note = "Funding Information: This work is part of the activities at the {\AA}bo Akademi Process Chemistry Group within the Finnish Centre of Excellence Programme (2000–2005) by the Academy of Finland. Financial support from the Raisio Group Research Foundation is gratefully acknowledged. The authors express their gratitude to Markku Reunanen for his contribution to the GC–MS analyses. Copyright: Copyright 2004 Elsevier Science B.V., Amsterdam. All rights reserved.",

year = "2003",

month = jun,

day = "10",

doi = "10.1016/S0926-860X(02)00646-4",

language = "English",

volume = "245",

pages = "257--275",

journal = "Applied Catalysis A: General",

issn = "0926-860X",

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T1 - Isomerization of linoleic acid over supported metal catalysts

AU - Bernas, Andreas

AU - Kumar, Narendra

AU - Mäki-Arvela, Päivi

AU - Kul'kova, Natalya V.

AU - Holmbom, Bjarne

AU - Salmi, Tapio

AU - Murzin, Dmitry Yu

N1 - Funding Information: This work is part of the activities at the Åbo Akademi Process Chemistry Group within the Finnish Centre of Excellence Programme (2000–2005) by the Academy of Finland. Financial support from the Raisio Group Research Foundation is gratefully acknowledged. The authors express their gratitude to Markku Reunanen for his contribution to the GC–MS analyses. Copyright: Copyright 2004 Elsevier Science B.V., Amsterdam. All rights reserved.

PY - 2003/6/10

Y1 - 2003/6/10

N2 - Heterogeneous supported metal catalysts were applied for the isomerization reaction of linoleic acid (cis-9,cis-12-octadecadienoic acid) to conjugated linoleic acid (CLA) between 80 and 120°C in a diluted system. Ru, Ni, Pd, Pt, Rh, Ir, Os, and bimetallic Pt-Rh supported by activated carbon, Al2O3, SiO2Al2O3, MCM-22, H-MCM-41, H-Y, and H-β were screened. Catalyst characterization was done by XRD, X-ray fluorescence, XPS, H2-TPD, DCP-AES, and nitrogen adsorption techniques. The isomerization reaction was conducted batchwise in both 1-octanol and n-decane as solvents. Reactions taking place were the isomerization of linoleic acid to CLA, hydrogenation of linoleic acid and CLA to monounsaturated octadecenoic acids (oleic acid, elaidic acid, cis-vaccenic acid, and trans-vaccenic acid), as well as the further hydrogenation of monounsaturated acids to stearic acid (n-octadecanoic acid) with isomerization and hydrogenation being two competing parallel reactions. The isomerization reaction was enhanced by catalyst preactivation under hydrogen. The presence of chemisorbed hydrogen increased the conversion but reduced the isomerization selectivity. Ru and Ni showed the best isomerization properties whereas Pd favored the double bond hydrogenation reaction.

AB - Heterogeneous supported metal catalysts were applied for the isomerization reaction of linoleic acid (cis-9,cis-12-octadecadienoic acid) to conjugated linoleic acid (CLA) between 80 and 120°C in a diluted system. Ru, Ni, Pd, Pt, Rh, Ir, Os, and bimetallic Pt-Rh supported by activated carbon, Al2O3, SiO2Al2O3, MCM-22, H-MCM-41, H-Y, and H-β were screened. Catalyst characterization was done by XRD, X-ray fluorescence, XPS, H2-TPD, DCP-AES, and nitrogen adsorption techniques. The isomerization reaction was conducted batchwise in both 1-octanol and n-decane as solvents. Reactions taking place were the isomerization of linoleic acid to CLA, hydrogenation of linoleic acid and CLA to monounsaturated octadecenoic acids (oleic acid, elaidic acid, cis-vaccenic acid, and trans-vaccenic acid), as well as the further hydrogenation of monounsaturated acids to stearic acid (n-octadecanoic acid) with isomerization and hydrogenation being two competing parallel reactions. The isomerization reaction was enhanced by catalyst preactivation under hydrogen. The presence of chemisorbed hydrogen increased the conversion but reduced the isomerization selectivity. Ru and Ni showed the best isomerization properties whereas Pd favored the double bond hydrogenation reaction.

KW - Conjugated linoleic acid (CLA)

KW - Double bond migration

KW - Functional food

KW - Hydrogenation

KW - Isomerization

KW - Linoleic acid

KW - Supported metal catalysts

UR - https://www.scopus.com/pages/publications/0037809698

U2 - 10.1016/S0926-860X(02)00646-4

DO - 10.1016/S0926-860X(02)00646-4

M3 - Article

AN - SCOPUS:0037809698

SN - 0926-860X

VL - 245

SP - 257

EP - 275

JO - Applied Catalysis A: General

JF - Applied Catalysis A: General

IS - 2

ER -

Isomerization of linoleic acid over supported metal catalysts

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