The Oxidation of 2,6-Di-tert-butyl-4-methylphenol<sup>1</sup>

Yohe, G. R.; Dunbar, Joseph E.; Pedrotti, Rudolph L.; Scheidt, Friedrich; Lee, Fred G. H.; Smith, Earle C.

doi:10.1021/jo01117a020

Cited by 34 publications

(12 citation statements)

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“…The 4-methyl group of 2,6-dialkyl-4-methylphenols can often be selectively oxidized to an aldehyde group [25]. The oxidation of 2,6-di-tert-butyl-4-methylphenol by oxidizing agents to 3,5-di-tert-butyl-4-hydroxybenzaldehyde has been described earlier [50]. In this study, the oxidized form was identified as main degradation product of Irganox 1222 ( Table 1, No.104).…”

Section: Decomposition Of Additivesmentioning

confidence: 99%

Thermal Stability of Polymer Additives: Comparison of Decomposition Models Including Oxidative Pyrolysis

Bartsch

Girard

Wilde

et al. 2018

Vinyl Additive Technology

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The thermo‐oxidative stability of widely used polymer additives has been investigated. A comparative analytical approach with classic and innovative decomposition models for polymer additives was conducted and the results supported using quantum‐chemical calculations. Unique pyrolysis products of the analytes were compiled utilizing pyrolysis online coupled to gas chromatography followed by mass spectrometric detection (Pyr‐GC–MS). The pyrolysis was either performed under inert conditions or in an oxygen‐containing atmosphere. Squalane was applied as polymer‐mimicking liquid next to low density polyethylene (LDPE) and polyamide 6 (PA 6) as matrices for 10 selected additives. The additives included in this study range from antioxidants and plasticizers to processing aids. These were selected to address a range of application in consumer products and to cover different chemical classes. The toxicological relevance of additives and potential breakdown products was considered. Consequently, degradation of sterically hindered antioxidants, diarylamines, and a trimellitic acid derivative was investigated. The findings were used to predict the behavior of consumer products made of polymeric materials entailing additives. The level of Antioxidant 2246 [2‐tert‐butyl‐6‐[(3‐tert‐butyl‐2‐hydroxy‐5‐methylphenyl)methyl]‐4‐methylphenol] and one of its predicted decomposition products was determined in baby bottle nipples made of natural rubber [2‐tert‐butyl‐4‐methylphenol] utilizing the complementary technique of gas chromatography coupled to tandem mass spectrometry (GC–MS/MS). This study provides a comprehensive characterization of important polymer additives and enables the prioritization of degradation products for further risk assessment. J. VINYL ADDIT. TECHNOL., 25:E12–E27, 2019. © 2018 The Authors. Journal of Vinyl and Additive Technology published by Wiley Periodicals, Inc. on behalf of Society of Plastics Engineers

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Section: Decomposition Of Additivesmentioning

confidence: 99%

Thermal Stability of Polymer Additives: Comparison of Decomposition Models Including Oxidative Pyrolysis

Bartsch

Girard

Wilde

et al. 2018

Vinyl Additive Technology

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“…Extraction of the products with aqueous sodium carbonate and acidification yielded a very small amount of a white precipitate from BMP but not from BP. This was identified by its melting point (134-135") as DL-trans-1,4-dioxo-5,6-di-t-butyl-2-hydroxy-2-cyclohexene (23). The ultraviolet spectra of the 168 hour BhIP sample showed a small unknown band a t 474 mp.…”

Section: Resultsmentioning

confidence: 99%

“…There have also been numerous studies in recent years of the products of oxidation of this pl~enol by a variety of oxidizing agents (18)(19)(20)(21)(22)(23)(24)(25). Some results on the reaction of t-butoxy radicals with 2,6-di-t-butylphenol (BP) are also reported.…”

Section: P Imentioning

confidence: 99%

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THE REACTION OF tert-BUTOXY RADICALS WITH 2,6-Di-tert-BUTYL-4-METHYLPHENOL AND 2,6-Di-tert-BUTYLPHENOL

Ingold¹

1963

Can. J. Chem.

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The products of the reaction of t-butowy radicals with 2,6-di-t-butyl-4-meth~lphei101 and 2,6-di-t-butplphenol ill carbon tetrachloride have been analyzed quantitatively. There is a satisfactory agreement between the measured and calculated yields of t-butanol u i t h both phenols. The deuterium isotope effect ( k~l k~) for abstraction of the pheilolic hydrogen from 2,6-di-t-butyl-4-methylphenol is about 6.4.The abstraction of hydrogen atoms by alkoxy radicals from substrates in the liquid phase is of particular interest in relation to autoxidation phenomena (1). These radicals are produced in the chain branching deco~llposition of the initially formed hydroperoxides and are therefore responsible for the autocatalytic nature of most autoxidations.The t-bu toxy radical is particularly suitable for studying the relative rates of reaction [2] with different substrates since it may either abstract a hydrogen to give t-butanol o r decdmpose t o give acetone and a methyl radical. The ratio, [t-butanol]/[acetone], produced in different substrates therefore gives a measure of the relative rates of hydrogen abstraction fro-m the substrates. These radicals are readily prepared by the decomposition of di-t-butyl peroxide and the reactions can be represented by, This technique has been employed by a number of workers in recent years to measure the relative rates of hydrogen abstraction by t-butoxy radicals from a variety of substrates such as hydrocarbons (2-9), ethers, (10, l l ) , alcohols (12), and amiiles (13,14). As a part of our general program for studying the inhibition of autoxidation by phenols (15-17) we considered that an examination of the reaction of t-butoxy radicals with phenols might throw considerable light on the overall mechanism of inhibition. In particular, we were interested to see whether the phenolic hydrogen was abstracted by the t-butoxy radical in the rate-determining step.In view of the comparative ease with which an isotope effect was detected in the reaction of peroxy radicals with 2,6-di-t-butyl-4-methylphenol (BLIP) (15, 16) this compound was chosen for the present investigation. There have also been numerous studies in recent years of the products of oxidation of this pl~enol by a variety of oxidizing agents (18)(19)(20)(21)(22)(23)(24)(25). Some results on the reaction of t-butoxy radicals with 2,6-di-t-butylphenol (BP) are also reported.

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“…acid, 2,6-di-(t-butyl)-benzo-quinone and 3,3',5,5'-tetra-(t-butyl)stilbene-4,4-quinone 16,17 were synthesized and isolated but their gas chromatographic retention times were different from the 5.4 minute of the impurity. When BHT was oxidized to 3,5-di-(t-butyl)-4-hydroxybenzaldehyde using bromine in t-butanol, the amount of the major impurity in the filtrate after the oxidation product had been collected, was about 30%.…”

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confidence: 99%

An Improved Preparation of 2,6-di-(t-Butyl)-4-methylphenol

Xie

Liu

Zhang

et al. 2015

Organic Preparations and Procedures International

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The Oxidation of 2,6-Di-tert-butyl-4-methylphenol¹

Cited by 34 publications

References 1 publication

Thermal Stability of Polymer Additives: Comparison of Decomposition Models Including Oxidative Pyrolysis

Thermal Stability of Polymer Additives: Comparison of Decomposition Models Including Oxidative Pyrolysis

THE REACTION OF tert-BUTOXY RADICALS WITH 2,6-Di-tert-BUTYL-4-METHYLPHENOL AND 2,6-Di-tert-BUTYLPHENOL

An Improved Preparation of 2,6-di-(t-Butyl)-4-methylphenol

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The Oxidation of 2,6-Di-tert-butyl-4-methylphenol1

Cited by 34 publications

References 1 publication

Thermal Stability of Polymer Additives: Comparison of Decomposition Models Including Oxidative Pyrolysis

Thermal Stability of Polymer Additives: Comparison of Decomposition Models Including Oxidative Pyrolysis

THE REACTION OF tert-BUTOXY RADICALS WITH 2,6-Di-tert-BUTYL-4-METHYLPHENOL AND 2,6-Di-tert-BUTYLPHENOL

An Improved Preparation of 2,6-di-(t-Butyl)-4-methylphenol

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The Oxidation of 2,6-Di-tert-butyl-4-methylphenol¹