RESUMEN
On July 11, 2003, the U.S. Food and Drug Administration (FDA) announced final regulations for trans fatty acid (TFA) labeling. By January 1, 2006, the TFA content of foods must be labeled as a separate line on the Nutrition Facts label. Products containing <0.5 g of TFA/14 g serving may be declared as zero. This paper describes technologies allowing compliance with TFA labeling requirements. Soybean oil was hydrogenated in a 2-L vessel at temperatures ranging from 120 to 170 degrees C at a hydrogen pressure of 200 psi. A commercial nickel-supported catalyst (25% Ni) was used at 0.02% Ni by weight of oil. The hydrogenated oils were characterized for fatty acid composition, solid fat content, and melting point. Compared to commercially processed soybean oil basestocks that typically contain approximately 40% TFA, those obtained at lower temperatures and higher pressures contain >56% less TFA. Basestocks prepared in the laboratory when blended with liquid soybean oil will yield spread oils meeting FDA labeling requirements for zero TFA, that is, <0.5 g of TFA/serving.
Asunto(s)
Manipulación de Alimentos/métodos , Etiquetado de Alimentos , Margarina/análisis , Aceite de Soja/química , Ácidos Grasos trans/análisis , Etiquetado de Alimentos/legislación & jurisprudencia , Hidrogenación , PresiónRESUMEN
The composition and structures of triacylglycerols (TAG) in a commercially prepared hydrogenated soybean oil margarine basestock [iodine value (IV) 65, 39.7% trans fatty acids] were determined by high-performance liquid chromatography (HPLC) in tandem with atmospheric pressure chemical ionization (APCI) mass spectrometry (MS). The basestock was separated by preparative HPLC into four fractions. Fractions 1 and 4, constituting approximately 8% of the total, were shown to consist of LOO, PLO, and LLS and OSS and PSS, respectively (where L = linoleic, O = oleic, S = stearic, and P = palmitic). APCI will not distinguish between O, oleic cis C18:1, and E, elaidic trans C18:1. Thus, O and E may be used interchangeably in discussion of TAG isomer structures. Fraction 2 consisted of OOO and POO. Fraction 3 consisted of OOO, POO, OOS, and POS. About 80% of the total triglycerides consisted of OOO, POO, and OOS. The trans fatty acid content of the fractions was determined, and the results showed that 92% of the total trans content was found in fractions 2 and 3. A shortening basestock (IV 81.7, 31.8% trans fatty acids) was partially characterized.
Asunto(s)
Margarina/análisis , Aceite de Soja/química , Triglicéridos/análisis , Triglicéridos/química , Presión Atmosférica , Cromatografía Líquida de Alta Presión/métodos , Hidrogenación , Espectrometría de Masas/métodosRESUMEN
Symmetrical disaturated triacylglycerols of the structure SUS, where S is stearic acid (18:0) and U is an unsaturated fatty acid, either oleic (O; 9cis-18:1), linoleic (L; 9cis,12cis-18:2), or linolenic (Ln; 9cis,12cis,15cis-18:3), are important components providing functionality to interesterified fat blends and structurally modified oils. Nonsymmetrical triacylglycerols of the structure SSU can significantly change melting point and solid fat content profiles. To characterize the physical properties of pure and symmetrical and nonsymmetrical triacylglycerol mixtures, the same reaction sequence has been used to prepare multigram quantities of triacylglycerols SUS and SSU. Tristearin was converted to a mixture of mono-, di-, and triacylglycerols, and the 1,3- and 1,2-diacylglycerol fraction was isolated by silica column chromatography. The 1,3-diacylglycerols were removed by crystallization from acetone and esterified with the appropriate fatty acid to form the symmetrical triacylglycerols with >99% SUS structure. The more difficult to obtain 1,2-diacylglycerols were prepared by esterification of the enriched 1,2-diacylglycerol fraction (80-86% 1,2-diacylglycerols) remaining after removal of much of the 1,3-isomer by crystallization, but silver resin or silver nitrate impregnated silica gel chromatography was required to isolate the nonsymmetrical triacylglycerols. SSL and SSLn were prepared in purities of >98% by this procedure, but not SSO. Silver ion HPLC was found to be as accurate as, and more rapid than, lipolysis/gas chromatography for the determination of the isomeric purities of the synthesized triacylglycerols.
Asunto(s)
Triglicéridos/análisis , Triglicéridos/síntesis química , Acetona , Cromatografía Líquida de Alta Presión , Cristalización , Diglicéridos/química , Esterificación , Ácido Linoleico/química , Ácido Oléico/química , Ácidos Esteáricos/química , Triglicéridos/química , Ácido alfa-Linolénico/químicaRESUMEN
A mathematical model was developed to describe the reduction of soybean oil triglycerides during hydrogenation. The model was derived from reaction and transport mechanisms and formulated into a system of first-order irreversible rate expressions that included terms for temperature, hydrogen pressure, and catalyst concentration. The model parameters were estimated from experimental data, and the model was used to simulate the results of hydrogenation performed over the pressure range of 0.069-6.9 MPa. The model could be extended to include geometrical isomers formed during hydrogenation.