707. Glyceride synthesis by direct esterification

Hartman, L.

doi:10.1039/jr9570003572

Cited by 39 publications

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“…We have found that a 24-hr reaction with monoglyceride and a 0.5 molar excess of pyridine and acid chloride gives maximum yield of 1,3-diglyceride. Based on the monoglyceride, the recoveries range from 60%-70% and are in agreement with those of Hartman (11).…”

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confidence: 84%

Synthesis of 100‐gram quantities of highly purified mixed acid triglycerides

Quinn

Sampugna

Jensen

1967

J Americ Oil Chem Soc

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Monopalmitin, mono-olein, and monostearin have been synthesized in quantities of up to 100 grams with recoveries ranging from 80%-85%. The monoglycerides were reacted with a 0.5 molar excess of pyridine and fatty acid chloride to produce 1, 3,-diglycerides. The recoveries ranged from 60%-70% and, in addition, considerable amounts of triglyceride were obtained from this reaction. Partial glycerides were converted to 100-gram batches of triglyceride in a similar manner with recoveries ranging from 80%-90%.Purification of the partial glycerides was achieved by crystallization. In addition to this technique, certain triglycerides were purified by elution through a column of alumina. Purity of the glyeerides, as determined by TLC, GLC, and pancreatic lipolysis, was estimated to be at least 99%.

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confidence: 84%

Synthesis of 100‐gram quantities of highly purified mixed acid triglycerides

Quinn

Sampugna

Jensen

1967

J Americ Oil Chem Soc

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“…Low values obtained by both the methods in some of the samples probably resulted from the impurities carried over during distillation. In order to find out if the earbonyl group present in the triglyceride molecules could be determined, triglycerides containing one or two moles of keto acids (12-oxo-9-cis-oetadecenoic acid) were prepared in the laboratory according to the method of Hartman (13). It has been shown that, during thermal oxidation of a fat, there is an increase in the carbonyl value (11).…”

Section: Resultsmentioning

confidence: 99%

“…Part of this attack takes place at the double bond, and some of the changes are also known to occur at the methylene group since the presence of a,f~-unsaturated carbonyl group has been demonstrated (12). In order to find out if the earbonyl group present in the triglyceride molecules could be determined, triglycerides containing one or two moles of keto acids (12-oxo-9-cis-oetadecenoic acid) were prepared in the laboratory according to the method of Hartman (13). These triglycerides and the keto acid were analyzed for the carbonyl content according to the modified procedure, and the results are presented in Table II.…”

Section: Resultsmentioning

confidence: 99%

A method for determining the carbonyl value in thermally oxidized fats

Bhalerao

Endres

Kummerow

1961

J Americ Oil Chem Soc

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A simple method for the determination of the earbonyl value of thermally oxidized fats, using hydroxylamine hydrochloride, is described. Normal octyl alcohol containing pyridine was used as a solvent, and the reaction was allowed to proceed at room temperature for 24 hrs. The titrations were carried out with the aid of a pH meter. The method was standardized against aliphatic aldehydes and ketones. The restflts of analyses showed that the different pure compounds reacted to an extent of 98% or better at room temperature.The method has been successfully applied for the deterruination of the earbonyl value of themnally oxidized fats. n-Valeric acid and the fatty acids with higher molecular weight were not found to interfere in the determination of the carbonyl value by the present method.NUIVIBER of analytical procedures for the determination of aldehydes and ketones, based on the use of hydroxylamine hydrochloride, have been reported. The amount of earbonyl oxygen present was quantitatively determined by estimating either the amount of unreaeted hydroxylaminc (1,2) or the amount of water formed during the reaction (3), or by estimating the hydrochloric acid liberated (4,5,6, 7,8). Lappin and Clark (9) have described a procedure which employs 2,4-dinitrophenylhydrazine for determining traces of carbonyls in aqueous or alcoholic solutions. This method with some modifications was employed by Heniek et al. (10) for the determination of carbonyls in rancid fats and foods. These analytical procedures were not found to be reliable for the quantitative determination of carbonyl oxygen in thernmtly oxidized fats because of their limited solubility in all but a few suitable solvents. A method for the determination of the carbonyl content of thermally oxidized fats, using hydroxylamine hydrochloride as a reagent and n-oetyl alcohol as a suitable solvent, is presented in this paper. Experimental ReagentsHydroxylamine Hydrochloride Reagent. Thirtyfive grams of hydroxylamine hydrochloride (reagent grade) were dissolved in 160 ml. of distilled water, and the resulting solution was diluted to 1 liter with 95% earbonyl-free ethyl alcohol.Standard Sodium Hydroxide in Methanol. Twenty grams of sodium hydroxide (analytical reagent) were dissolved in a small amount of water and diluted to 1 liter with absolute methyl alcohol and standardized against standard hydrochloric acid (0.5 N).Pyridinc-octyl Alcohol Solvent. Five ml. of pyridine (analytical reagent) were diluted to 1 liter wth n-octyl alcohol.A Beeknlan ptI meter, Laboratory Model H2, equipped with standard glass electrode and standard calomel electrode, wtcs used in this work. Analytical ProcedureOne gram of the sample to be analyzed was weighed into a 250-ml. glass-stoppered Erlenmeyer flask. Fifty ml. of pyridine-oetyl alcohol solvent were pipetted into it, and, if necessary, the flask was heated on a hot plate until the sample was dissolved. Fifteen ml. of hydroxylamine hydrochloride reagent was then added with a pipette. The flask was stoppered, the contents were mixed we...

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“…Trilaurin, trimyristin, tripalmitin, and tristearin calibration standards of greater than 99% purity were purchased from Applied Science Laboratories, State College, Pa. Triolein, triarachidin, and tribehenin standards of 99% purity were purchased from the Hormel Institute, Austin, Minn. A synthetic mixture of C45, C46, C~7, and C~8 triglycerides was prepared by reacting equal molar quantifies of pentadecanoyl and palmitoyl chlorides with glycerol as described by Hartman (13).…”

Section: Methodsmentioning

confidence: 99%

Gas‐liquid chromatography of triglyceride mixtures containing both odd and even carbon number fatty acids

Litchfield¹,

Harlow

Reiser

1967

Lipids

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Quantitative GLC of triglycerides has been extended to natural fats containing both odd and even carbon number fatty acids. A 1.83-m glass column containing 3.0% JXR silicone on 100/120 mesh Gas-Chrom Q resolved triglycerides differing by only one carbon number. Peak resolution was significantly improved by hydrogenating each triglyceride sample prior to GLC analysis.The triglycerides of four fish oils (mullet, tuna, menhaden, and pilchard) and one seed fat (Acanthosyris spinescens) containing odd carbon number fatty acids were analyzed by this technique. The method was also useful for determining the triglyceride composition of the cyclopentene fatty acid oil fromHydnocarpus wightiana seeds.

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707. Glyceride synthesis by direct esterification

Cited by 39 publications

References 0 publications

Synthesis of 100‐gram quantities of highly purified mixed acid triglycerides

Synthesis of 100‐gram quantities of highly purified mixed acid triglycerides

A method for determining the carbonyl value in thermally oxidized fats

Gas‐liquid chromatography of triglyceride mixtures containing both odd and even carbon number fatty acids

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