Occurrence, detection, and prevention of cyclization during hydrogenation of fatty oils

Coenen, J. W. E.; Wieske, Th.; Cross, RF; Rinke, Miss H.

doi:10.1007/bf02582656

Cited by 25 publications

(3 citation statements)

References 18 publications

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“…However, natural sources for aromatic fatty acids are scarce in the plant kingdom. In addition, the fatty acid pattern in these plants was different to our samples (e.g., only the odd-chained Ph-11:0, Ph-13:0, 15-phenylpentadecanoic acid (Ph-15:0), 13-phenyltridecenoic acid (Ph-13:1) and 15-phenylpentadecenoic acid (Ph-15:1) were detected in Arum maculatum [25] ). This rather pointed towards the formation of the aromatic fatty acids in the rumen of the cows.…”

Section: Discussioncontrasting

confidence: 92%

“…Different fatty acids with the aromatic moiety in the chain (terminal carbons in the ortho-position: 1, 2, 3, 4, 5, 6, 8) have been identified as artefacts of the industrial hydrogenation (with a palladium or nickel catalyst) of unsaturated cyclic acids derived from the alkali treatment of linseed oil at temperatures above 200°C [24,25,39,40]. Although these conditions were different to those occurring in the rumen of cows we could not fully rule out this opportunity, since the mass spectra of the methyl esters of some aromatic fatty acid artefacts published by Zeman et al were quite similar to the spectra recorded in our samples (they featured M ?…”

Section: Resultsmentioning

confidence: 99%

“…These have been described in plants of the aroid subfamily [16][17][18][19], Dracunculus vulgaris, i.e., a flowering plant in the family Araceae (in samples from Turkey, 13-phenyltridecanoic acid (Ph-13:0) was found to contribute about 10 % to the total fatty acids [20,21] ), in Brazilian plants of the Trichilia genus [22], as well as a bacterium (Vibrio alginolyticus) associated with the marine alga Cladophora coelothrix [23]. In addition, isomers with the phenyl unit in the acyl chain are formed as artefacts during the hydrogenation of plant oils [24][25][26][27]. Since this process is similar to the function of the rumen of cows, both structural variants of aromatic fatty acids could be the origin of the potentially aromatic fatty acids detected in the milk fat of a butter sample.…”

Section: Introductionmentioning

confidence: 99%

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Identification of Aromatic Fatty Acids in Butter Fat

Schröder

Abdurahman

Ruoff

et al. 2014

J Americ Oil Chem Soc

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Bovine milk fat contains a large variety of structurally different fatty acids. In this study, we describe the presence of aromatic fatty acids in a butter fat sample. Fatty acids were released from butter fat and converted into the corresponding methyl esters (FAME). Urea complexation was used to separate the main saturated fatty acids. GC/MS screening of the FAME in the filtrate of the urea complexation indicated the presence of aromatic fatty acids. By (1) conversion of two representatives into picolinyl esters which were analyzed by GC/MS, (2) linear log t R over carbon number plots (R 2 = 0.95) and by the use of two reference standards we were able to show that the phenyl unit was located on the terminal carbon of the straight acyl chain of the FAME. In a fraction gathered by countercurrent chromatography we were able to identify 3-phenylpropionic acid (Ph-3:0), 4-phenylbutyric acid (Ph-4:0), 5-phenylpentanoic acid (Ph-5:0), 6-phenylhexanoic acid (Ph-6:0), 7-phenylheptanoic acid (Ph-7:0), 8-phenyloctanoic acid (Ph-8:0), 9-phenylnonanoic acid (Ph-9:0), 10-phenyldecanoic acid (Ph-10:0), 11-phenylundecanoic acid (Ph-11:0), 12-phenyldodecanoic acid (Ph-12:0), 13-phenyltridecanoic acid (Ph-13:0), along with one unsaturated phenyldecenoic acid (Ph-10:1) isomer. Preliminary results indicate that the aromatic fatty acids may have been formed exogenously in the rumen of the cows. The total amount of the aromatic fatty acids was estimated at 0.15 mg/g butter fat, which corresponds with an average daily intake of *5 mg per day in Germany and *4.4 mg per day in Europe.

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Section: Discussioncontrasting

confidence: 92%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Identification of Aromatic Fatty Acids in Butter Fat

Schröder

Abdurahman

Ruoff

et al. 2014

J Americ Oil Chem Soc

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Bildung aromatischer Carbonsäuren bie der Alkali‐Cyclisierung langkettiger Triencarbonsäuren

Sagredos

Scharmann

Wolf

1973

Justus Liebigs Ann. Chem.

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Bei der Alkali-Cyclisierung von Octadecatriencarbonsauren entstehen aus den intermediaren c~:-(2-Alkylcyclohexadienyl)alkancarbonsauren mono-und disubstituierte Benzolderivate. Diese Reaktion ist nicht von der alkalischen Katalyse abhangig, sondern nur von der Temperatur. Bei 220" C oder mehr werden die ~:-(2-Alkylcyclohexadienyl)alkancarbonsauren (1, Schema 1) zum Teil in (c-(0-Alkylpheny1)alkancarbonsauren (9) und in c+(2-Alkylcyclohexeny1)alkancarbonsauren (8) disproportioniert und zum Teil unter Wasserstoffabspaltung sowie intramolekularer Abspaltung ihrer Alkyl-oder co-Alkancarbonsaure-Gruppen zu 9 und den homologen o!-Phenylalkancarbonsauren (10) sowie Alkylbenzolen (12) aromatisiert. Bei niedrigeren Temperaturen entstehen als einzige Aromatisierungsprodukte die disubstituierten Benzolderivate 9. Formation of Aromatic Carboxylic Acids in the Alkali Cyclisation of Long-Chain Trienoic AcidsIn the alkali cyclisation of octadecatrienoic acids the intermediate w-(2-alkylcyclohexadienyl)-alkanecarboxylic acids form mono-and disubstituted benzene derivatives. This reaction does not depend on the presence of the alkaline catalyst but on thermal conditions. At temperatures of 220" C or more, one part of the w-(2-alkylcyclohexadienyl)alkanecarboxylic acids disproportionates to form w-(0-alkylpheny1)alkanecarboxylic acids (9) and w-(2-alkylcyclohexenyl)-alkanecarboxylic acids (8), while the other part loses hydrogen and alkyl or w-alkanecarboxy groups to yield compounds of type 9 as well as the homologous w-phenylalkanecarboxylic acids (10) and alkylbenzenes (12). At lower temperatures, the only aromatization products detected were disubstituted benzene derivatives 9.Bei der Umsetzung von Octadecatriencarbonsauren mit Alkali fallen neben w-(2-Alkylcyclohexadienyl)alkancarbonsauren und Cyclohexen-Derivaten mit konjugierter semicyclischer Doppelbindung in geringen Mengen w-(o-Alkylpheny1)alkancarbonsauren (9) und w-Phenylalkancarbonsauren (10) an 1-3). Dabei steigt der Anteil der aromatischen Carbonsauren 9 laut 1R-Spektrum mit der Zeit auf Kosten der ~( 2 -Alky 1cyclohexadienyl)alkancarbonsauren an 1).Um den Entstehungsmechanismus dieser aromatischen Verbindungen zu untersuchen, wurde als Modellsubstanz eine Mischung von w-(2-A1kylcyclohexadienyl)-alkancarbonsauren der Strukturen 1, 2 und 3 verwendet, wie sie bei der Cyclisierung von 9=, 1 It, 13*-Octadecatriensaure (7) mit NaOH/Diathylenglykol bei 220°C nach einer Reaktionsdauer von 20 min anfallt 1).

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Bestimmung aromatischer Fettsäuren in hydrierten cyclischen Fettsäuren

Eckert

1968

Fette, Seifen, Anstrichm.

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Occurrence, detection, and prevention of cyclization during hydrogenation of fatty oils

Cited by 25 publications

References 18 publications

Identification of Aromatic Fatty Acids in Butter Fat

Identification of Aromatic Fatty Acids in Butter Fat

Bildung aromatischer Carbonsäuren bie der Alkali‐Cyclisierung langkettiger Triencarbonsäuren

Bestimmung aromatischer Fettsäuren in hydrierten cyclischen Fettsäuren

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