Analysis of Mixtures of Aldehydes and Ketones

Gordon, B. E.; Wopat, F.; Burnham, H. D.; Jones, L. C.

doi:10.1021/ac60060a009

Cited by 65 publications

(27 citation statements)

References 21 publications

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“…Chromatography ( 15,37,43) and infrared spectra of derivatives (41) can be used to identify reaction products, but results are complicated by the fact that glycols (42) and a-hydroxyketones (29), under certain conditions, may be oxidized to ketone derivatives by 2,4-dinitrophenylhydrazine. A typical run is described below.…”

Section: Figure 1 Modified Parr Apparatusmentioning

confidence: 99%

Hydrogen Peroxide Reactions with Olefins

Norton¹,

White²

1965

Advances in Chemistry

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The osmium tetroxide-catalyzed addition of hydrogen peroxide to olefins has been reinvestigated with innovations of reagents, catalyst, and procedures to obtain product analyses and material balances for the hydrogen peroxide consumption. Significant amounts of carbonyl by-products-acetol, organic acids, peracids, and possibly pyruvaldehyde-are formed under the range of conditions studied. Experimental design studies of the effects of reaction variables upon yields of the various products under batch and continuous addition conditions have been completed. The nature of the catalytic complex involved in the initiation of the reaction is reviewed. The order and rate of product appearance does not support a simple oxidation sequence. A branching reaction sequence consistent with experimental results is proposed.uydrogen peroxide is becoming less expensive and has been used for the " liquid-phase oxidation of olefins (7,21,22,23,24,26,34,38,39); but its use in oxidizing gaseous olefins has not received much attention. We have investigated its use in oxidizing gaseous olefins, especially propylene, noting in particular the glycol and by-product yields obtained.A review of the chemical literature (1,2,5,16,20,30,40) and laboratory experiments confirmed that the Milas reagent ( 14,19,21,22,23,24,26,28 ), osmium tetroxide in f erf-butyl alcohol, is one of the more effective catalysts for liquid-phase oxidation.

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Section: Figure 1 Modified Parr Apparatusmentioning

confidence: 99%

Hydrogen Peroxide Reactions with Olefins

Norton¹,

White²

1965

Advances in Chemistry

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“…The product (66.5 mg) contained: C, 64.7%; H , 8.1%; N, 12.7%. C12H18x202 requires: C, 64.8%; H, 8.27,; K, 12.67,. The compound was insoluble in water and very slightly soluble in organic solvents a t room temperature.…”

Section: Reduction Of Pz~dcherviininic Acid With Phosphorus and Iodinmentioning

confidence: 99%

“…60-80" C). The petroleum ether e x t r a~t s were evaporated to dryness and the solid chromatographed on a silicic acid -celite column (8). The first colored band, eluted from the column with 2% ether in petroleum ether, was collected, the solvent evaporated off, and the solid recrystallized twice from petroleum ether.…”

Section: Reduction Of Pz~dcherviininic Acid With Phosphorus and Iodinmentioning

confidence: 99%

The Structure of Pulcherriminic Acid

MacDonald¹

1963

Can. J. Chem.

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The red pigment pulcherrimin was isolated from three strains of Candida pulcher~ima and converted to pulcherritninic acid. The properties of derivatives of this acid and the products obtained from its reduction indicate that it differs from pulcherriminic acid isolated by other ~vorkers. probable structure for the new pulcherriminic acid is 2,5-diisobutyl-3,6-dihydroxypyra~ine-l,4-dioxide. The structures of the compounds obtained from its reduction were also in\ estigated. INTRODUCTIOS

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“…Acetaldehyde 2,4-dinitrophenylhydrazone was the main product of these changes but formaldehyde and other 2,4-dinitrophenylhydrazones were also obtained. The proportion changed was greater when relatively small amounts of the 2,4-dinitrophenylhydrazone were applied to the column, and the effect was much more marked on silica gel than on alumina.Since alumina and silica gel columns have been widely used for the fractionation of 2,4-dinitrophenylhydreaones (Gordon et al 1951) and since further work on mixtvres of aliphatic carbonyl compounds was contemplated in this laboratory, a study was made of the factors responsible for these changes.Use of ethanol in place of ether, use of other brands of silica gel, washing the gel with hydrochloric acid to remove iron, and extensive washing with water to remove hydrochloric acid, all failed to suppress the changes.It is poasible that 2,4-dinitrophenylhydrazones and carbonyl compounds present in the solvents enter into an exchange reaction, but then the use of carbonyl-free solvents should suppress the changes, but this was not so.There exists the possibility that carbonyl compounds are produced during the passage of the solvent through the column and, while the reason for this …”

mentioning

confidence: 99%

“…Since alumina and silica gel columns have been widely used for the fractionation of 2,4-dinitrophenylhydreaones (Gordon et al 1951) and since further work on mixtvres of aliphatic carbonyl compounds was contemplated in this laboratory, a study was made of the factors responsible for these changes.…”

mentioning

confidence: 99%

Change of 2,4-Dinitrophenylhydrazones on alumina and silica gel chromatographic columns

Forss¹,

Dunstone²

1957

Aust. J. Chem.

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I n an investigation of the " cardboard " flavour in skim milk (Forss, Pont, and Stark 1955a, 1955b), the compounds responsible for this defect were found to be the C,-,, 2-enals and the 0,-,, 2,4-dienals. These unsaturated aldehydes were separated by passing their 2,4-dinitrophenylhydrazones through chromatographic columns. While these derivatives passed unchanged through alumina and silica gel columns when developed with ether and light petroleum, some of the 2,4-dinitrophenylhydraeones of the aliphatic saturated aldehydes and ketones which were also present were observed to change. Acetaldehyde 2,4-dinitrophenylhydrazone was the main product of these changes but formaldehyde and other 2,4-dinitrophenylhydrazones were also obtained. The proportion changed was greater when relatively small amounts of the 2,4-dinitrophenylhydrazone were applied to the column, and the effect was much more marked on silica gel than on alumina.Since alumina and silica gel columns have been widely used for the fractionation of 2,4-dinitrophenylhydreaones (Gordon et al. 1951) and since further work on mixtvres of aliphatic carbonyl compounds was contemplated in this laboratory, a study was made of the factors responsible for these changes.Use of ethanol in place of ether, use of other brands of silica gel, washing the gel with hydrochloric acid to remove iron, and extensive washing with water to remove hydrochloric acid, all failed to suppress the changes.It is poasible that 2,4-dinitrophenylhydrazones and carbonyl compounds present in the solvents enter into an exchange reaction, but then the use of carbonyl-free solvents should suppress the changes, but this was not so.There exists the possibility that carbonyl compounds are produced during the passage of the solvent through the column and, while the reason for this

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Analysis of Mixtures of Aldehydes and Ketones

Cited by 65 publications

References 21 publications

Hydrogen Peroxide Reactions with Olefins

Hydrogen Peroxide Reactions with Olefins

The Structure of Pulcherriminic Acid

Change of 2,4-Dinitrophenylhydrazones on alumina and silica gel chromatographic columns

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