Chromato–Mass Spectrometric Identification of Unusual Products of 4-Isopropylphenol Oxidation in Aqueous Solutions

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Chromato–Mass Spectrometric Identification of Unusual Products of 4-Isopropylphenol Oxidation in Aqueous Solutions. / Зенкевич, Игорь Георгиевич ; Пушкарева, Татьяна Ивановна.

в: Russian Journal of General Chemistry, Том 88, № 1, 01.01.2018, стр. 7-14.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

BibTeX

@article{070ecd9101b94819ac2896bc1895da5f,

title = "Chromato–Mass Spectrometric Identification of Unusual Products of 4-Isopropylphenol Oxidation in Aqueous Solutions",

abstract = "4-Isopropylphenol has been chosen as the simplest object to model the processes of oxidation of organic compounds with air oxygen in aqueous media, since it contains a hydrogen atom at the tertiary carbon atom in the α-position with benzene ring and a hydroxyl group enabling mass-spectrometric detection of the products in the negative ions mode. It has been stated that oxidation of 4-isopropylphenol with air oxygen in aqueous media becomes noticeable as the solution pH approaches the рK а value of the substrate (10.25). The major product [4-isopropyl-2-(4-isopropylphenoxy)phenol] is formed via nucleophilic addition of the starting 4-isopropylphenol at the intermediate product of its oxidation, quinone methide. Intensity of electrochemical oxidation can be tubed by changing the electrode potential. The highest conversion of 4-isopropylphenol has been observed at potential 1.5–3.0 V, the formed compounds being the products of transformation of the same quinone methide intermediate. The obtained data have explained the formation and diversity of dimeric and oligomeric products of oxidation of natural flavonoids. ",

keywords = "4-isopropylphenol, aqueous media, dissolved air oxygen, electrochemical oxidation, free-radical oxidation, quinone methides",

author = "Зенкевич, {Игорь Георгиевич} and Пушкарева, {Татьяна Ивановна}",

year = "2018",

month = jan,

day = "1",

doi = "10.1134/S1070363218010024",

language = "English",

volume = "88",

pages = "7--14",

journal = "Russian Journal of General Chemistry",

issn = "1070-3632",

publisher = "МАИК {"}Наука/Интерпериодика{"}",

number = "1",

}

RIS

TY - JOUR

T1 - Chromato–Mass Spectrometric Identification of Unusual Products of 4-Isopropylphenol Oxidation in Aqueous Solutions

AU - Зенкевич, Игорь Георгиевич

AU - Пушкарева, Татьяна Ивановна

PY - 2018/1/1

Y1 - 2018/1/1

N2 - 4-Isopropylphenol has been chosen as the simplest object to model the processes of oxidation of organic compounds with air oxygen in aqueous media, since it contains a hydrogen atom at the tertiary carbon atom in the α-position with benzene ring and a hydroxyl group enabling mass-spectrometric detection of the products in the negative ions mode. It has been stated that oxidation of 4-isopropylphenol with air oxygen in aqueous media becomes noticeable as the solution pH approaches the рK а value of the substrate (10.25). The major product [4-isopropyl-2-(4-isopropylphenoxy)phenol] is formed via nucleophilic addition of the starting 4-isopropylphenol at the intermediate product of its oxidation, quinone methide. Intensity of electrochemical oxidation can be tubed by changing the electrode potential. The highest conversion of 4-isopropylphenol has been observed at potential 1.5–3.0 V, the formed compounds being the products of transformation of the same quinone methide intermediate. The obtained data have explained the formation and diversity of dimeric and oligomeric products of oxidation of natural flavonoids.

AB - 4-Isopropylphenol has been chosen as the simplest object to model the processes of oxidation of organic compounds with air oxygen in aqueous media, since it contains a hydrogen atom at the tertiary carbon atom in the α-position with benzene ring and a hydroxyl group enabling mass-spectrometric detection of the products in the negative ions mode. It has been stated that oxidation of 4-isopropylphenol with air oxygen in aqueous media becomes noticeable as the solution pH approaches the рK а value of the substrate (10.25). The major product [4-isopropyl-2-(4-isopropylphenoxy)phenol] is formed via nucleophilic addition of the starting 4-isopropylphenol at the intermediate product of its oxidation, quinone methide. Intensity of electrochemical oxidation can be tubed by changing the electrode potential. The highest conversion of 4-isopropylphenol has been observed at potential 1.5–3.0 V, the formed compounds being the products of transformation of the same quinone methide intermediate. The obtained data have explained the formation and diversity of dimeric and oligomeric products of oxidation of natural flavonoids.

KW - 4-isopropylphenol

KW - aqueous media

KW - dissolved air oxygen

KW - electrochemical oxidation

KW - free-radical oxidation

KW - quinone methides

UR - http://www.scopus.com/inward/record.url?scp=85042845267&partnerID=8YFLogxK

U2 - 10.1134/S1070363218010024

DO - 10.1134/S1070363218010024

M3 - Article

VL - 88

SP - 7

EP - 14

JO - Russian Journal of General Chemistry

JF - Russian Journal of General Chemistry

SN - 1070-3632

IS - 1

ER -

ID: 34723364