The Condensation of Aminoantipyrine. Vi. A Study of the Effect of Excess Base on the Reaction of Amino-Antipyrine With Phenolic Compounds in the Presence of Oxidizing Agents

Emerson, Edgar; Kelly, K. W.

doi:10.1021/jo01162a008

Cited by 32 publications

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“…Description of colorimetric assay. Condensation of 4-aminoantipyrine with a phenol in the presence of alkaline oxidizing agents produces a red antipyrine dye (AAPPC) in what is known as the Emerson reaction (4,5). This reaction is more sensitive than other color reactions of phenols (16).…”

Section: Methodsmentioning

confidence: 99%

Assay for detection and enumeration of genetically engineered microorganisms which is based on the activity of a deregulated 2,4-dichlorophenoxyacetate monooxygenase

King

Short

Seidler

1991

Appl Environ Microbiol

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An assay system was developed for the enumeration of genetically engineered microorganisms expressing a deregulated 2,4-dichlorophenoxyacetate (TFD) monooxygenase, which converts phenoxyacetate (PAA) to phenol. In PAA-amended cultures of Pseudomonas aeruginosa PAO1C(pRO103) and Pseudomonas putida PPO301(pRO103), strains which express a deregulated TFD monooxygenase, phenol production was proportional to cell number. Phenol was reacted, under specific conditions, with a 4-aminoantipyrine dye to form an intensely colored dye-phenol complex (AAPPC), which when measured spectrophotometrically could detect as few as 103 cells per ml. This assay was corroborated by monitoring the disappearance of PAA and the accumulation of phenol by high-performance liquid chromatography and gas chromatography. The AAPPC assay was modified for use with plate cultures and clearly distinguished colonies of PPO301(pRO103) and PAOlC(pRO103) from a strain expressing a regulated TFD monooxygenase. Colonies of P. putida PPO301(pRO101) remained cream colored, while colonies of PPO301(pRO103) and PAO1C(pRO103) turned a distinct red.

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Section: Methodsmentioning

confidence: 99%

Assay for detection and enumeration of genetically engineered microorganisms which is based on the activity of a deregulated 2,4-dichlorophenoxyacetate monooxygenase

King

Short

Seidler

1991

Appl Environ Microbiol

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“…The method here described is a combination of the bromine turbidimetric method described by Shaw (5,6) and a procedure using 4-aminoantipyrine, which was originally suggested and studied by Emerson (2,3) for the determination of phenol. APPARATUS A steam cabinet is required, preferably a copper can 150 X 100 X 250 mm.…”

Section: Determination Of Phenols In Aqueous Wastesmentioning

confidence: 99%

Determinations of Phenols in Aqueous Wastes from Coke Plants

Shaw¹

1951

Anal. Chem.

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E. Add 10 ml. of 2.0% potassium ferricyanide solution to all portions and mix immediately. F. Immediately pour 100 ml. of the sample and the 0.2 p.p.m. standard into individual 100-ml. Nessler tubes.If the sample does not show more red color than the standard, consolidate the entire sample portion and put it in a 1-liter separatory funnel. Put the blank and the 0.04 p.p.m. standard in 1-liter separatory funnels. Extract these solutions serially with 15-, 10-, and 5-ml.portions of chloroform. Combine the extracts and make them up to 25 ml. with chloroform. Filter the extracts before volume adjustment if high precision or high sensitivity is required.G. Read the optical density of both the 0.04 p.p.m. standard and the sample at 460 µ against the blank extract.If the optical density of 5 cm. of liquid is over 1.0, base comparisons on readings made using 1-cm. tubes.H. Compute the phenol content on a proportional basis, as the reaction is linear.I. If at step D the sample is darker than the 0.20 standard, start comparisons immediately using the aqueous solutions. Read both the sample and the 1.0 p.p.m. standard against the aqueous blank at 510 µ and calculate the phenol content of the sample on a proportional basis.SUMMARY Investigation of the reaction between 4-aminoantipyrine and phenols for analytical purposes indicates the following factors to be significant:The reaction products may be concentrated by extraction with chloroform in the case of all phenols investigated. The red aqueous dyes are extracted with chloroform to yield orange or yellow solutions. Serial extractions may be so arranged that the extraction is substantially quantitative and a large concentration factor is obtained.The aqueous reaction mixture is unstable. When allowed to stand, the color produced by the reaction of phenol and 4-amino-antipyrine fades. Concurrently, the color due to the reagents increases.

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“…phenolic pollutants is desirable. Since 1965, the 4-aminoantipyrine (4-AAP) assisted chromogenic reaction driven by K 3 Fe(CN) 6 has became a standard method [15][16][17][18][19][20] for phenolic compounds detection [19,20]. Though the K 3 Fe(CN) 6 -based chromogenic reaction is fast and has high conversion efficiency under mild conditions, the necessary oxidant K 3 Fe(CN) 6 is toxic and unstable when exposed to sunlight or mixed with acid/alkali substance.…”

Section: Introductionmentioning

confidence: 99%

A magnetically recyclable Fe3O4@C@TNCuPc composite catalyst for chromogenic identification of phenolic pollutants

Huang³

et al. 2015

Journal of Molecular Catalysis A: Chemical

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The Condensation of Aminoantipyrine. Vi. A Study of the Effect of Excess Base on the Reaction of Amino-Antipyrine With Phenolic Compounds in the Presence of Oxidizing Agents

Cited by 32 publications

References 0 publications

Assay for detection and enumeration of genetically engineered microorganisms which is based on the activity of a deregulated 2,4-dichlorophenoxyacetate monooxygenase

Assay for detection and enumeration of genetically engineered microorganisms which is based on the activity of a deregulated 2,4-dichlorophenoxyacetate monooxygenase

Determinations of Phenols in Aqueous Wastes from Coke Plants

A magnetically recyclable Fe3O4@C@TNCuPc composite catalyst for chromogenic identification of phenolic pollutants

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