2,6-Di-tert-butyl-1,4-benzoquinone

220.3074

220.31

211-946-0

4C9D8L0Y0T

14448

DTXSID7021493

Yellow crystals

2914690090

34.1

4.42

Solid

1.0±0.1 g/cm3

65-67 °C

65-67 °C @ Press: 1 Torr

106.2±17.4 °C

1.504

Insoluble in water.

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

II; III

4.1

NONH for all modes of transport

3

R36/37/38

S26-S36-S36/37/39-S22

DK3970000

Xi:Irritant

Stable under normal temperatures and pressures.

P261-P305 + P351 + P338

H315-H319-H335

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 46 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

1 of 21 samples of wastewater from the photographic industry contained unreported concentrations of 2,6-di-t-butyl-p-benzoquinone(1). 1 of 10 POTW plants sampled contained 2,6-di-t-butyl-p-benzoquinone in the final effluent(2).

2,6-Di-t-butyl-p-benzoquinone was present in Pawtuxet River sediment located downstream of a plant which produced antioxidants (at concentrations of 1 ppm to 80 ppm(1). 2,6-Di-t-butyl-p-benzoquinone was present in sediment (0.1-40 ppm) located downstream from a specialty chemicals manufacturing plant(2).

URBAN/SUBURBAN: 2,6-Di-t-butyl-p-benzoquinone was detected in the personal air (1 of 8 samples total) of 12 people located either in New Jersey or North Carolina(1).

VOLATILE POLLUTANTS, INCLUDING 2,6-DI-T-BUTYL-P-BENZOQUINONE, WERE PRODUCED FROM SEVERAL RUBBER GOODS MANUFACTURING PROCESSES & ANALYZED BY GAS CHROMATOGRAPHY/MASS SPECTROMETRY. THEIR CUMULATIVE CONCN RANGED FROM 25-27,000 UG/CU M.|2,6-Di-t-butyl-p-benzoquinone's production and subsequent use as an oxidant and polymerization catalyst(1), may result in its release to the environment through various waste streams(SRC). 2,6-Di-t-butyl-p-benzoquinone is also an environmental product of the oxidation of 2,6-di-t-butyl phenol, a common antioxidant additive(2,3).

TERRESTRIAL FATE: Based on a recommended classification scheme(3), an estimated Koc value of 6000(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(1), indicates that suggests that 2,6-di-t-butyl-p-benzoquinone will be essentially immobile in soil(3). In an unconfined aquifer, however, 2,6-di-t-butyl-p-benzoquinone was transported an estimated 2710 meters over a 43 year period(2,4). 2,6-Di-t-butyl-p-benzoquinone is not expected to volatilize from moist soil surfaces based on an estimated Henry's Law constant of 1.6X10-8 atm-cu m/mole(5,SRC). It may, however, volatilize from the surface of dry soils given an estimated vapor pressure of 4.1X10-4 mm Hg(6,SRC). Incomplete information is available regarding the biodegradation potential of 2,6-di-t-butyl-p-benzoquinone; Rhine River water which was subjected to bank filtration had lower concentrations of 2,6-di-t-butyl-p-benzoquinone than the original water(7). Adsorption to soil however, was not measured(7,SRC)).|AQUATIC FATE: 2,6-Di-t-butyl-p-benzoquinone should adsorb to suspended solids and organic matter in the water column based on an estimated Koc of 6100(1,SRC) from an experimental log Kow(2) and a suggested classification scheme(3). 2,6-Di-t-butyl-p-benzoquinone (at 0.3 ug/L) had a half-life in Rhine River water of 3.4 days; measurements were made at Lobith and 24.5 hours later at Gorinchem(4). Loss of this compound during this stretch of river may have been due to adsorption to particulates or to biodegradation(4,SRC). An estimated BCF value of 1400(1,SRC), from an experimental log Kow(2), suggests that 2,6-di-t-butyl-p-benzoquinone will bioconcentrate in aquatic organisms. This compound has been detected in fish from the Great Lakes(5). 2,6-Di-t-butyl-p-benzoquinone is not expected to volatilize from water surfaces based on an estimated Henry's Law constant of 1.6X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(6).|ATMOSPHERIC FATE: Based on an estimated vapor pressure of 4.1X10-4 mm Hg at 25 °C(1,SRC), 2,6-di-t-butyl-p-benzoquinone should exist in both the vapor phase and particulate phase in the ambient atmosphere(2,SRC). 2,6-Di-t-butyl-p-benzoquinone should degrade in the vapor phase by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 17 hours(3,SRC). Particulate-phase 2,6-di-t-butyl-p-benzoquinone may be physically removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor phase reaction of 2,6-di-t-butyl-p-benzoquinone with photochemically produced hydroxyl radicals has been estimated as 2.23X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). The half-life of 2,6-di-t-butyl-p-benzoquinone would be approximately 17 hours based on a hydroxyl radical concentration of 5X10+5 per cu cm(1,SRC).

An estimated BCF value of 1400 was calculated for 2,6-di-t-butyl-p-benzoquinone, using a measured log Kow of 4.42(1) and a recommended regression-derived equation(2,SRC). This BCF value suggests that 2,6-di-t-butyl-p-benzoquinone will bioconcentrate in aquatic organisms(2,SRC).This compound was detected in fish in the Great Lakes(3) suggesting that bioconcentration may occur(SRC).

Based on an experimental log Kow of 4.42(1), the Koc of 2,6-di-t-butyl-p-benzoquinone is estimated as approximately 6100 using a regression-derived equation(2,SRC). According to a suggested classification scheme(3), this estimated Koc value suggests that 2,6-di-t-butyl-p-benzoquinone will be immobile in soil(SRC). Sewage which had been through secondary treatment was subjected to rapid infiltration; the concentration of 2,6-di-t-butyl-p-benzoquinone in the initial sewage was from 0.022-0.037 ug/L and ranged from barely detected to 0.005 ug/L in the groundwater below the rapid infiltration beds(4). It was believed that the loss of this compound was due to adsorption as the sewage had already been through secondary treatment(4). In an unconfined aquifer, however, 2,6-di-t-butyl-p-benzoquinone was shown to have been transported for a considerable distance(between 1940-1983, estimated 2710 m)(1,5).

The Henry's Law constant for 2,6-di-t-butyl-p-benzoquinone is estimated as 1.6X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This indicates that 2,6-di-t-butyl-p-benzoquinone will essentially not volatilize from water surfaces(2,SRC).

SURFACE WATER: 2,6-Di-t-butyl-p-benzoquinone, present at 2 ug/L in Rhine River water, was almost completely removed during bank filtration(1). 2,6-Di-t-butyl-p-benzoquinone was present in both wastewater (0.01-0.02 ppm) from a specialty chemicals manufacturing plant and in river water downstream from this plant (concentration = 0.001-0.011 ppm)(2).|DRINKING WATER: 2,6-Di-t-butyl-p-benzoquinone was detected in tap water from Tsukuba, Japan at unreported concentrations(1). 2,6-Di-t-butyl-p-benzoquinone was detected in drinking water in 1 of 5 US cities (Miami, FL) at 0.1 ug/L(2). 3 of 3 water supply plants in the New Orleans, LA area had 2,6-di-t-butyl-p-benzoquinone present in their finished drinking water (concentrations = 0.19-0.23 ppb)(3).|GROUNDWATER: Rapid infiltration of primary wastewater from Fort Devens, MA, containing non-detectable quantities of 2,6-di-t-butyl-p-benzoquinone resulted in this chemical appearing in one of two down-gradient wells (concentration = 0.034 ug/L)(1). 2,6-Di-t-butyl-p-benzoquinone present at concentrations of 0.022-0.037 ug/L in sewage from Phoenix, AZ was subjected to rapid infiltration; groundwater samples beneath the rapid infiltration beds indicated the presence of this compound but at barely detectable quantities(2). 2,6-Di-t-butyl-p-benzoquinone was detected in the groundwater beneath 4 of 4 land application (of primary wastewater) sites (Ft Devens, MA; Boulder, CO = 1.51 ug/L; Lubbock, TX; Phoenix,AZ)(3).|GROUNDWATER: 2,6-Di-t-butyl-p-benzoquinone was detected in contaminated groundwater at Otis Air Base, MA, at a concentration of 390 ng/L(1). 2,6-Di-t-butyl-p-benzoquinone was detected in groundwater under a municipal landfill in Oklahoma(2). Groundwater from the Edwards aquifer contained 2,6-di-t-butyl-p-benzoquinone in two of 5 wells at approximately 10-30 ng/L(3).

2,6-Di-t-butyl-p-benzoquinone was detected in the water supply (1 of 1 sample total) of 12 people located either in New Jersey or North Carolina(1).

THE URINARY & FECAL EXCRETION OF 3 NEW METABOLITES OF BUTYLATED HYDROXYTOLUENE (BHT, 3,5-DI-TERT-BUTYL-4-HYDROXYTOLUENE) WERE REVEALED BY GAS CHROMATOGRAPHY AFTER IP ADMIN TO MALE WISTAR RATS. THE STRUCTURES OF THESE METABOLITES, 2,6-DI-TERT-BUTYL-P-BENZOQUINONE, 2,6-DI-TERT-BUTYLHYDROQUINONE, & 2,6-DI-TERT-BUTYL-4-((METHYLTHIO)METHYL)PHENOL WERE IDENTIFIED BY COMPARISON OF GAS CHROMATOGRAPHIC & MASS SPECTRAL DATA WITH THOSE OF AUTHENTIC SAMPLES.|Quinones (ie, 6,12-dione) have been shown to undergo oxidation-reduction cycles involving quinone, hydroquinone, and molecular oxygen, resulting in the formation of oxygen radicals and semiquinone radicals. /Quinones/

Chronic neurotoxic effects include vision disturbances. /From table/ /Quinones/

2,6-di-tert-butyl-4-benzoquinone

2,5-Cyclohexadiene-1,4-dione, 2,6-bis(1,1-dimethylethyl)-: ACTIVE

2,6-Di-t-butyl-p-benzoquinone was measured in municipal incinerator flyash following extraction and capillary GC/MS.

2,6-Di-t-butyl-p-benzoquinone was measured in fish using open-column chromatography followed by GC/MS.