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Changes in chemical composition of catalytically hydrogenated orange oil ( Citrus sinensis )

Identifieur interne : 003422 ( Main/Exploration ); précédent : 003421; suivant : 003423

Changes in chemical composition of catalytically hydrogenated orange oil ( Citrus sinensis )

Auteurs : Elena E. Stashenko [Colombie] ; Ramiro Martínez [Colombie] ; M. Helena Pinz N [Colombie] ; Jesús Ramírez [Colombie]

Source :

Journal of Chromatography A [ 0021-9673 ] ; 1996.

RBID : ISTEX:B5CFA2D3019407D85A4D7798FAEC3F7F67FB846F

Descripteurs français

Pascal (Inist)
- Agrume, Analyse chimique, Chromatographie phase gazeuse, Citrus sinensis, Composition chimique, Détecteur ionisation flamme, Huile essentielle, Hydrogénation, Monoterpène, Méthode couplée, Orange, Spectrométrie masse.
Wicri :
- topic : Agrume, Huile essentielle.

English descriptors

KwdEn :
- Chemical analysis, Chemical composition, Citrus fruit, Citrus sinensis, Coupled method, Essential oil, Flame ionization detector, Gas chromatography, Hydrogenation, Mass spectrometry, Monoterpene, Orange.

Abstract

Orange oil obtained from fresh fruit peels by cold pressing was subjected to hydrogenation at 60, 70 and 80°C and 0.46 MPa (H2 pressure) over Adam's catalyst (PtO2 at 0.5 and 0.75%, w/w). The chemical composition of neat and hydrogenated oil was established by high-resolution gas chromatography (HRGC) with flame ionization (FID) and mass spectrometric (MS) detection. The principal components of orange oil were monoterpenes (limonene 94.00%, α-pinene 0.54%, sabinene 0.74%, ß-myrcene 1.18%), followed by oxygenated compounds such as alcohols (linalool 0.89% and α-terpineol 0.06%) and aldehydes (citral-Z 0.09%, citral-E 0.14%, citronellal 0.07%). HRGC-FID-MS analysis of the hydrogenated mixtures revealed the presence of over twenty components, mainly the products of hydrogenation of limonene, citral, linalool, ß-myrcene, sabinene and ß-ocimene. α-Pinene and aliphatic aldehydes did not react under these conditions. The appearance of α-terpinolene and the increase of γ-terpinene concentration from 0.05% to 0.15% in the modified oils indicated isomerization associated with hydrogenation. Citral (E- and Z-) was converted into citronellal (0.06–0.12%) and dihydrocitronellal (0.06–0.16%). Linalool was transformed into 3,7-dimethyl-1-octen-3-ol (0.42–0.63%) and 3,7-dimethyloctan-3-ol (0.11–0.32%). Various isomers formed by H2 addition to the endo and exo double bonds in limonene constituted the main products (up to 95%) in the hydrogenated orange oils. The concentration of hydrogenated products increased from 62.78 to 89.76% when the temperature dropped from 80 to 60°C at a catalyst concentration of 0.5% (w/w). A smaller change was observed with 0.75% (w/w) catalyst.

Url:

https://api.istex.fr/document/B5CFA2D3019407D85A4D7798FAEC3F7F67FB846F/fulltext/pdf

DOI: 10.1016/S0021-9673(96)00481-5

Affiliations:

Colombie

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<front><div type="abstract" xml:lang="en">Orange oil obtained from fresh fruit peels by cold pressing was subjected to hydrogenation at 60, 70 and 80°C and 0.46 MPa (H2 pressure) over Adam's catalyst (PtO2 at 0.5 and 0.75%, w/w). The chemical composition of neat and hydrogenated oil was established by high-resolution gas chromatography (HRGC) with flame ionization (FID) and mass spectrometric (MS) detection. The principal components of orange oil were monoterpenes (limonene 94.00%, α-pinene 0.54%, sabinene 0.74%, ß-myrcene 1.18%), followed by oxygenated compounds such as alcohols (linalool 0.89% and α-terpineol 0.06%) and aldehydes (citral-Z 0.09%, citral-E 0.14%, citronellal 0.07%). HRGC-FID-MS analysis of the hydrogenated mixtures revealed the presence of over twenty components, mainly the products of hydrogenation of limonene, citral, linalool, ß-myrcene, sabinene and ß-ocimene. α-Pinene and aliphatic aldehydes did not react under these conditions. The appearance of α-terpinolene and the increase of γ-terpinene concentration from 0.05% to 0.15% in the modified oils indicated isomerization associated with hydrogenation. Citral (E- and Z-) was converted into citronellal (0.06–0.12%) and dihydrocitronellal (0.06–0.16%). Linalool was transformed into 3,7-dimethyl-1-octen-3-ol (0.42–0.63%) and 3,7-dimethyloctan-3-ol (0.11–0.32%). Various isomers formed by H2 addition to the endo and exo double bonds in limonene constituted the main products (up to 95%) in the hydrogenated orange oils. The concentration of hydrogenated products increased from 62.78 to 89.76% when the temperature dropped from 80 to 60°C at a catalyst concentration of 0.5% (w/w). A smaller change was observed with 0.75% (w/w) catalyst.</div>
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Changes in chemical composition of catalytically hydrogenated orange oil ( Citrus sinensis )

Changes in chemical composition of catalytically hydrogenated orange oil ( Citrus sinensis )

Source :

Descripteurs français

English descriptors

Abstract

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