http://dspace.uniten.edu.my/jspui/bitstream/123456789/3506/1/Understanding%20the%20chemistry%20behind%20the%20antioxidant%20activities%20of%20butylated%20hydroxytoluene%20%28BHT%29-%20A%20review.pdf

Understanding the chemistry behind the antioxidant activities of butylated hydroxytoluene (BHT): a review.

Palladium‐ and Nickel‐Catalyzed Synthesis of Sodium Acrylate from Ethylene, CO2, and Phenolate Bases: Optimization of the Catalytic System for a Potential Process

2,6-Di-tert-butyl-4-methylene-2,5-cyclohexadienone: a hepatic metabolite of butylated hydroxytoluene in rats.

The selective oxidation of 2,3,6-trimethylphenol (TMP) and 2-methyl-1-naphthol (MNL) with H2O2 catalyzed by titanium single-site catalysts, TiO2–SiO2 aerogel and mesostructured hydrothermally stable titanium-silicate, Ti-MMM-2, have been studied by means of EPR spectroscopic technique with spin traps. The formation of phenoxyl (naphthoxyl) and hydroxyl radical intermediates during the oxidation process have been detected using 3,5-dibromo-4-nitrosobenzene-sulfonic acid (DBNBS) and 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) spin traps, respectively. The character of the EPR spectra of the DBNBS adducts strongly depends on the nature of the organic substrate and the reaction temperature. A compilation of the EPR and by-product studies strongly supports a homolytic oxidation mechanism. Study by DR-UV–vis spectroscopy has confirmed the previously suggested chemical adsorption of phenol on the titanium center.

EPR study on the mechanism of H2O2-based oxidation of alkylphenols over titanium single-site catalysts

https://link.springer.com/content/pdf/10.1016%2Fj.jasms.2005.02.009.pdf

Mass spectral fragmentation of the intravenous anesthetic propofol and structurally related phenols.

Sterically hindered phenols: Communication 6. Bromination of 2,6-dialkyl-p-cresols and 2,6-dialkyl-4-(bromomethyl)phenols

1.

A method was developed for the synthesis of 4-substituted 2,6-di-t-butylphenols by the reduction of the corresponding quinols with lithium aluminum hydride.




2.

Some new inhibitors of free-radical reactions were prepared, and some of their properties were studied.

Sterically hindered phenols

The reactions of sterically hindered phenols (phenoxides) and their derivatives (phenoxy-radicals and cyclohexadienones), in the first step of which the transfer of one electron is possible, have been examined. To confirm the hypothesis concerning the mechanism of organic reactions with transfer of one electron, kinetic data and the results of the polarographic analysis and investigation of the reactions under discussion by physicochemical methods are presented. Certain reactions of sterically hindered phenols and their derivatives the investigators of which supported previously a different mechanism have been analysed critically from the standpoint of the mechanism involving the transfer of one electron. The bibliography includes 124 references.

Reactions of Sterically Hindered Phenols and Their Derivatives with Transfer of one Electron

Sodium (1) and potassium (2) 1-(carboxy)-1-(N-methylamide)-2-(3′,5′-di-tert-butyl)-4-hydroxyphenyl)-propionates form crystal hydrates, which exist as both monomers and dimers. Quantum-chemical calculations in the PM6 approximation are used to determined the enthalpies of formation −Hfpo, thermal enthalpy Hpo, and entropy Spo of the monomers and dimers, which are indicative of the possibility of existence of the dimers of propionates of alkali metals. The biological activity of these compounds in animal and plants is demonstrated to be dependent on their concentrations. Compounds 1 and 2 turned out to be efficient in the treatment of burn injuries, cancer, and radiation damage (in vivo and in vitro), as well as in promoting the growth of cereal plants.

Structure and biological properties of sodium and potassium 1-(carboxy)-1-(N-methylamide)-2-(3′,5′-di-tert-butyl)-4-hydroxyphenyl)-propionates

The crucial factor of the reaction of 2,6-di-tert-butylphenol with alkali hydroxides is temperature, depending on which two types of potassium or sodium 2,6-di-tert-butylphenoxides are formed. These types exhibit different catalytic activity in the alkylation of 2,6-di-tert-butylphenol with methyl acrylate. More active forms of 2,6-But
2C6H3OK or 2,6-But
2C6H3ONa are synthesized at temperatures higher than 160 °C and are predominantly the monomers, which dimerize on cooling. The data of 1H NMR, electronic, and IR spectra for the corresponding forms of 2,6-But
2C6H3OK and 2,6-But
2C6H3ONa isolated in the individual state are in agreement with cyclohexadienone structure. In DMSO or DMF, the dimeric forms of 2,6-di-tert-butylphenoxides react with methyl acrylate to form methyl 3-(4-hydroxy-3,5-di-tert-butylphenyl)propionate in 64–92% yield.

http://ena.lp.edu.ua:8080/bitstream/ntb/8008/1/03.pdf

A. A. Volod'kin

Papers

Sterically hindered phenols: Communication 6. Bromination of 2,6-dialkyl-p-cresols and 2,6-dialkyl-4-(bromomethyl)phenols

Sterically hindered phenols

Reactions of Sterically Hindered Phenols and Their Derivatives with Transfer of one Electron

Structure and biological properties of sodium and potassium 1-(carboxy)-1-(N-methylamide)-2-(3′,5′-di-tert-butyl)-4-hydroxyphenyl)-propionates

Potassium and sodium 2,6-di-tert-butylphenoxides and their properties