Selective Enrichment of Conjugated Linoleic Acid Isomers in Their Mixtures Using Combined Chemical and Enzymatic Methods

Jiwon Kim, Min Yu Chung, Hee Don Choi, In Wook Choi, In-Hwan Kim, Hyang Sook Chun, Byung Hee Kim

Research output: Contribution to journalArticle

Abstract

The aim of this study was to selectively enrich t10,c12-conjugated linoleic acid (t10,c12-CLA) and c9,t11-CLA in commercial CLA mixtures using a combination of urea crystallization and lipase-catalyzed esterification. The objective of the urea fractionation is to remove saturated and monounsaturated fatty acids (FA) from the CLA mixtures. CLA-enriched free FA (FFA) mixtures containing 53.8 wt% t10,c12-CLA and 39.1 wt% c9,t11-CLA were produced from the CLA mixtures containing ~34 wt% each of the two CLA isomers by a urea crystallization using methanol and the urea-to-FA weight ratio of 2.5:1. The CLA-enriched FFA mixtures were partially esterified with dodecan-1-ol in a recirculating packed-bed reactor using an immobilized lipase from Candida rugosa to further enrich the t10,c12-CLA and c9,t11-CLA in an FFA fraction and an FA dodecyl ester fraction, respectively, under the optimal conditions, i.e., temperature, 20 °C; FA-to-dodecan-1-ol molar ratio, 1:1; water content, 2 wt% of total substrates; residence time, 5 min; and reaction time, 24 h (for t10,c12-CLA enrichment) and 12 h (for c9,t11-CLA enrichment). After the reaction, an FFA fraction with 72.6 wt% t10,c12-CLA was obtained. Another FFA fraction with 62.0 wt% c9,t11-CLA was recovered after the saponification of the FA dodecyl ester fraction. The yields of t10,c12-CLA and c9,t11-CLA in the FFA fractions were 43.6 and 21.5 wt%, respectively, based on their initial weights in the CLA mixtures.

Original languageEnglish
Pages (from-to)577-585
Number of pages9
JournalJAOCS, Journal of the American Oil Chemists' Society
Volume94
Issue number4
DOIs
Publication statusPublished - 2017 Apr 1

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Linoleic acid
Conjugated Linoleic Acids
Isomers
Fatty Acids
Fatty acids
Urea
Lipases
Crystallization
Lipase
Esters
Monounsaturated fatty acids
Saturated fatty acids
Saponification
Monounsaturated Fatty Acids
Candida
Esterification
Packed beds
Fractionation
Water content
Methanol

Keywords

  • Candida rugosa lipase
  • cis-9,trans-11 Conjugated linoleic acid
  • Esterification
  • Recirculating packed-bed reactor
  • trans-10,cis-12 Conjugated linoleic acid
  • Urea crystallization

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Organic Chemistry

Cite this

Selective Enrichment of Conjugated Linoleic Acid Isomers in Their Mixtures Using Combined Chemical and Enzymatic Methods. / Kim, Jiwon; Chung, Min Yu; Choi, Hee Don; Choi, In Wook; Kim, In-Hwan; Chun, Hyang Sook; Kim, Byung Hee.

In: JAOCS, Journal of the American Oil Chemists' Society, Vol. 94, No. 4, 01.04.2017, p. 577-585.

Research output: Contribution to journalArticle

Kim, Jiwon ; Chung, Min Yu ; Choi, Hee Don ; Choi, In Wook ; Kim, In-Hwan ; Chun, Hyang Sook ; Kim, Byung Hee. / Selective Enrichment of Conjugated Linoleic Acid Isomers in Their Mixtures Using Combined Chemical and Enzymatic Methods. In: JAOCS, Journal of the American Oil Chemists' Society. 2017 ; Vol. 94, No. 4. pp. 577-585.
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abstract = "The aim of this study was to selectively enrich t10,c12-conjugated linoleic acid (t10,c12-CLA) and c9,t11-CLA in commercial CLA mixtures using a combination of urea crystallization and lipase-catalyzed esterification. The objective of the urea fractionation is to remove saturated and monounsaturated fatty acids (FA) from the CLA mixtures. CLA-enriched free FA (FFA) mixtures containing 53.8 wt{\%} t10,c12-CLA and 39.1 wt{\%} c9,t11-CLA were produced from the CLA mixtures containing ~34 wt{\%} each of the two CLA isomers by a urea crystallization using methanol and the urea-to-FA weight ratio of 2.5:1. The CLA-enriched FFA mixtures were partially esterified with dodecan-1-ol in a recirculating packed-bed reactor using an immobilized lipase from Candida rugosa to further enrich the t10,c12-CLA and c9,t11-CLA in an FFA fraction and an FA dodecyl ester fraction, respectively, under the optimal conditions, i.e., temperature, 20 °C; FA-to-dodecan-1-ol molar ratio, 1:1; water content, 2 wt{\%} of total substrates; residence time, 5 min; and reaction time, 24 h (for t10,c12-CLA enrichment) and 12 h (for c9,t11-CLA enrichment). After the reaction, an FFA fraction with 72.6 wt{\%} t10,c12-CLA was obtained. Another FFA fraction with 62.0 wt{\%} c9,t11-CLA was recovered after the saponification of the FA dodecyl ester fraction. The yields of t10,c12-CLA and c9,t11-CLA in the FFA fractions were 43.6 and 21.5 wt{\%}, respectively, based on their initial weights in the CLA mixtures.",
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AB - The aim of this study was to selectively enrich t10,c12-conjugated linoleic acid (t10,c12-CLA) and c9,t11-CLA in commercial CLA mixtures using a combination of urea crystallization and lipase-catalyzed esterification. The objective of the urea fractionation is to remove saturated and monounsaturated fatty acids (FA) from the CLA mixtures. CLA-enriched free FA (FFA) mixtures containing 53.8 wt% t10,c12-CLA and 39.1 wt% c9,t11-CLA were produced from the CLA mixtures containing ~34 wt% each of the two CLA isomers by a urea crystallization using methanol and the urea-to-FA weight ratio of 2.5:1. The CLA-enriched FFA mixtures were partially esterified with dodecan-1-ol in a recirculating packed-bed reactor using an immobilized lipase from Candida rugosa to further enrich the t10,c12-CLA and c9,t11-CLA in an FFA fraction and an FA dodecyl ester fraction, respectively, under the optimal conditions, i.e., temperature, 20 °C; FA-to-dodecan-1-ol molar ratio, 1:1; water content, 2 wt% of total substrates; residence time, 5 min; and reaction time, 24 h (for t10,c12-CLA enrichment) and 12 h (for c9,t11-CLA enrichment). After the reaction, an FFA fraction with 72.6 wt% t10,c12-CLA was obtained. Another FFA fraction with 62.0 wt% c9,t11-CLA was recovered after the saponification of the FA dodecyl ester fraction. The yields of t10,c12-CLA and c9,t11-CLA in the FFA fractions were 43.6 and 21.5 wt%, respectively, based on their initial weights in the CLA mixtures.

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