Notes- Reduction of Phenols to Aromatic Hydrocarbons

Moulton, Wilbur N.; Wade, Clarence W. R.

doi:10.1021/jo01351a601

Cited by 11 publications

(4 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The mass balance curves for all acidic pH tests showed a continuous decline, whereas no additional and/or significant peaks were observed in the mass spectra. Hence, benzene, the end product from phenol reduction, is likely to be responsible for the decline in the curve, but it degraded rapidly and could not be detected because the photodecay rate coefficient of benzene is very close to that of phenol (i.e., about 3 × 10 −4 s −1 , data not shown). In addition, the rupture of the aromatic ring or ring contraction may also be responsible for the decline .…”

Section: Resultsmentioning

confidence: 99%

Photochemical Degradation of 2,4,6-Trichlorophenol in the Brij 35 Micellar Solution: pH Control on Product Distribution

Chu

Rao

Kwan

et al. 2009

Ind. Eng. Chem. Res.

View full text Add to dashboard Cite

Surfactants have been used for separating organic pollutants from contaminated soils in soil-washing process. The extracted pollutants can be effectively degraded upon UV irradiation in the presence of surfactant micelles. The photodecay rate of 2,4,4, by UV light at 253.7 nm and photonic efficiency of 2,4,6-TCP degradation reaction were investigated at different pH levels with the addition of nonionic surfactant solutions above the critical micelle concentration (cmc). A continual examination on intermediates at all pHs was conducted and photochemical processes induced the dechlorination of TCP to form di-and monochlorinated intermediates and phenol. An additional reaction was observed when the initial pH level was above neutral, at which chlorinated hydroquinones were the resulting intermediates through photohydrolysis process. Two reaction mechanisms, one at acidic and the other at basic conditions, were proposed and verified by the evidence presented in this study.

show abstract

Section: Resultsmentioning

confidence: 99%

Photochemical Degradation of 2,4,6-Trichlorophenol in the Brij 35 Micellar Solution: pH Control on Product Distribution

Chu

Rao

Kwan

et al. 2009

Ind. Eng. Chem. Res.

View full text Add to dashboard Cite

show abstract

“…Since the ring-mass was composed of the residual of 2,4-D and aromatic derivatives in the solution, the fractions of lost ring-mass in low (0.63) and high pH levels (0.19) indicate the levels of ring-opening formation of nondetectable aromatic end-products. Benzene is likely to be one of such compounds, because the reduction of phenol to benzene is possible as justified by Moulton and Wade 4 Formation and destruction of the reaction products of 2,4-D photolysis in Brij 35 micellar solution at initial pH of 2.98.…”

Section: Resultsmentioning

confidence: 99%

Reaction Mechanism of Photoreduction of 2,4-Dichlorophenoxyacetic Acid in Surfactant Micelles

Kwan

Chu

2005

Ind. Eng. Chem. Res.

View full text Add to dashboard Cite

The direct photolysis of 2,4-dichlorophenoxyacetic acid (2,4-D) in water is slow and ineffective, but surfactant micelles can greatly enhance the photochemical reaction of organic contaminants. The effect of an anionic (sodium dodecyl sulfate), a cationic (cetyltrimethylammonium bromide), and two nonionic (Brij 35, Tween 80) surfactants on the phototransformation of 2,4-D at 253.7 nm was examined. Except for the anionic surfactant, the other micelles were significant facilitators in both removal efficiencies and decay rates of 2,4-D. This herbicide was then irradiated in the presence of Brij 35 micelles at five different initial pH levels. 2,4-D is an organic acid, and its speciation (molecular or ionic form) is controlled by pH. It was found that the photoreduction of 2,4-D was more effective at lower initial pH than that in basic conditions. The transformation of 2,4-D in micelles occurred predominantly through reductive chlorination, resulting in generation of less chlorinated products. The presence of hydroxylated products in low yields indicated photohydrolysis was a minor competitive reaction pathway. The measurable intermediates were 2-chlorophenoxyacetic acid, 4-chlorophenoxyacetic, chlorohydroxyphenoxyacetic acid, phenoxyacetic acid, hydroxyphenyoxyacetic acid, and phenol. The transformed products were identified by comparing the HPLC retention times of the standards, and confirmed by LC-MS.

show abstract

“…Rei der Rrduktion von 2 b init I>& und Phenol iiach MOULTOX und \~~A D E [8) entsteht 2-Phenyl -naphthalin.…”

unclassified

“…In Gegenwart von Phenylacetylen bildet sich p-~itroplienylessigsaure-~7-nitro-5-phenyl-naphthyl-( l)]-ester 2 d in 67proz. Ausbeutc (Xylol,8…”

unclassified

Zur Bildung von Phenyl‐naphtholen‐(1) bei der Thermolyse von Phenylacetylchloriden in Gegenwart von Phenylacetylen

1973

View full text Add to dashboard Cite

Beim Erhitzen von Phenylacetylchlorid auf 170–180°C bzw. von p‐Nitrophenylacetylchlorid auf 140°C erfolgt intramolekulare Chlorwasserstoff‐Abspaltung unter Bildung des in Substanz nicht beständigen Phenylketens bzw. p‐Nitrophenylketens, das in situ an Phenylacetylen als Ketenfänger addiert wird. Die nicht faßbaren Cycloadditionsprodukte isomerisieren sich über Zwischenstufen zu stabilen Phenyl‐naphtholen‐(1), die unter den Reaktionsbedingungen zu entsprechenden Phenylessigsäureestern acyliert werden. Analog verläuft die Thermolyse von Diphenylacetylchlorid.

show abstract

Notes- Reduction of Phenols to Aromatic Hydrocarbons

Cited by 11 publications

References 1 publication

Photochemical Degradation of 2,4,6-Trichlorophenol in the Brij 35 Micellar Solution: pH Control on Product Distribution

Photochemical Degradation of 2,4,6-Trichlorophenol in the Brij 35 Micellar Solution: pH Control on Product Distribution

Reaction Mechanism of Photoreduction of 2,4-Dichlorophenoxyacetic Acid in Surfactant Micelles

Zur Bildung von Phenyl‐naphtholen‐(1) bei der Thermolyse von Phenylacetylchloriden in Gegenwart von Phenylacetylen

Contact Info

Product

Resources

About