General Description
A yellowish-colored crystalline solid with a pungent, irritating odor. Poisonous by ingestion or inhalation of vapors. May severely damage skin, eyes and mucous membranes. Used to make dyes and as a photographic chemical.
Reactivity Profile
BENZOQUINONE acts as an oxidizing agent .
Air & Water Reactions
Soluble in water and denser than water. If moist BENZOQUINONE(106-51-4) may decompose spontaneously above 140°F. This has occurred in drums, causing over-pressurization.
Hazard
Toxic by inhalation, strong irritant to skin,
eyes and mucous membranes. Skin damage. Ques-
tionable carcinogen.
Health Hazard
Poisonous; may be fatal if inhaled, swallowed or absorbed through the skin. Contact with solid, vapor or solution can cause severe local damage to the skin and mucous membranes. Symptoms include discoloration, severe irritation, erythema, swelling, papules and vesicles. Necrosis may result from long exposure. The eyes may experience irritation, conjunctivitis, photophobia, lacrymation and burning sensations. The cornea may suffer ulceration and scarring. Chronic eye exposure causes gradual brownish discoloration of the conjunctiva and cornea, small corneal opacities and damage in corneal structure which cause loss of visual acuity.
Potential Exposure
Due to this compound’s ability to
react with certain nitrogen compounds to form colored sub-
stances, quinone is widely used in the dye, textile, chemi-
cal, tanning, and cosmetic industries. It is used as an
industrial chemical; laboratory reagent; and as an interme-
diate in chemical synthesis for hydroquinone and other
chemicals.
First aid
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately. If
this chemical has been inhaled, remove from exposure, begin
rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medi-
cal attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit.
Shipping
UN2587 Benzoquinone, Hazard Class: 6.1;
Labels: 6.1-Poisonous materials.
Incompatibilities
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explo-
sions. Keep away from alkaline materials, strong bases, strong
acids, oxoacids, epoxides, some combustible substances;
reducing agents. Decomposes exothermically on warming
above 60 ? C, when moist, producing carbon monoxide.
Chemical Properties
Quinone is a yellow, crystalline material or large yellow, monoclinic prisms. Pungent, irritating odor.
1,4-Benzoquinone or p-benzoquinone is the basic structure of quinonoid compounds.They are widely distributed in the natural world, being found in bacteria, plants and arthropods and hence quinones are ubiquitous to living systems. Quinones play pivotal role in biological functions including oxidative phosphorylation and electron transfer.
Waste Disposal
Controlled incineration
(982℃, 2.0 seconds minimum).
Physical properties
Light yellow crystals with an acrid odor resembling chlorine. Odor threshold concentration is 84
ppb (quoted, Amoore and Hautala, 1983).
Uses
1,4-Benzoquinone is used in the manufactureof dyes, fungicide, and hydroquinone; fortanning hides; as an oxidizing agent; and inphotography.
Uses
As an oxidizing agent; in photography;
tanning hides; intermediate in the manufacturing
of dyes, fungicides, and hydroquinone.
Uses
Oxidizing agent; in photography; manufacture of dyes; manufacture of hydroquinone; tanning hides; making gelatin insoluble; strengthening animal fibers; as reagent.
Application
p-Benzoquinone is used as a dienophile in Diels-Alder cycloadditions to prepare naphthoquinones and 1,4-phenanthrenediones. It acts as a dehydrogenation reagent and an oxidizer in synthetic organic chemistry. In the Thiele-Winter reaction, it is involved in the preparation of triacetate of hydroxyquinol by reacting with acetic anhydride and sulfuric acid. It is also used in the synthesis of bromadol and to suppress double- bond migration during olefin metathesis reactions. It is used as a precursor to hydroquinone which finds application in photography and as a reducing agent and an antioxidant in rubber production.
Definition
ChEBI: The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.
Production Methods
Quinone was produced as early as 1838 by oxidation of quinic acid with manganese dioxide. Quinone can be prepared by oxidation starting with aniline or by the oxidation of hydroquinone with bromic acid. More recently, quinone has been made biosynthetically from D-glucose.
Reactions
1,4-Benzoquinone and its derivatives are extensively used in Diels-Alder reactions. A facile tautomerization of alkyl substituted 1,4-benzoquinone to o-quinone methide is the highlight of this cycloaddition.
Diels-Alder reaction of 1,4-benzoquinone with thiophene dioxide by Kang et al.
Fire Hazard
Noncombustible solid; ignition can occur
after only moderate heating, autoignition
temperature 560°C (1040°F); fire-extinguishing
agent: water spray. 1,4-Benzoquinone
may react violently with strong oxidizers,
especially at elevated temperatures.
Carcinogenicity
Quinone has been tested for
carcinogenicity in mice by skin application or inhalation
and in rats by subcutaneous injection. None of these
studies were considered sufficient to evaluate carcinogenicity
(335, 336). A cancer bioassay of Tribolium-infested flour
has been conducted but lack of quantification of quinone
and methodological issues make the data difficult to
interpret.
Quinone has produced negative results in studies designed
to examine its ability to promote carcinogenicity. In a liver
bioassay, quinone did not increase the formation of GGTpositive
foci in the liver. Quinone did not promote
induction of stomach or skin tumors in mice dosed with 7,12-
dimethylbenzanthracene.
Environmental Fate
Quinone exists in the atmosphere in the gas phase. The
dominant atmospheric loss process for quinone is expected to
be by reaction with the hydroxyl (OH) radical (reaction with
ozone is expected to be slow because of the >C(O) substituent
groups). The estimated half-life and lifetime of quinone in the atmosphere due to reaction with the OH radical are w3 and
4 h, respectively. Release of 1,4-benzoquinone to the environment
occurs via its effluents during its commercial
production and use and in wastewaters from the coal industry.
If released to soil, it is likely to leach (estimated Koc of 30) and
may volatilize and photodegrade on soil surfaces. The ambient
atmospheric concentration of 1,4-benzoquinone has been reported
to be less than 15–80 ng m-3, and benzoquinone has
been detected in tobacco smoke.
Purification Methods
Purify p-benzoquinone in one or more of the following ways: steam distillation followed by filtration and drying (e.g. in a desiccator over CaCl2), crystallisation from pet ether (b 80-100o), *benzene (with, then without, charcoal), water or 95% EtOH, sublimation under vacuum (e.g. from room temperature to liquid N2). It slowly decomposes and should be stored, refrigerated, in an evacuated or sealed glass vessel in the dark. It should be resublimed before use. [Wolfenden et al. J Am Chem Soc 109 463 1987, Beilstein 7 IV 2065.]
Toxicity evaluation
The acute narcotic effects are due to the physical interaction of
quinone itself on the cells of the central nervous system (CNS).
The long-term effects are most likely due to the production of
an unstable reactive intermediate during biotransformation or
redox cycling. Cytochrome P450–mediated xenobiotic metabolism
often leads to biological intermediates with attributes
identical to quinones.
