Quinone

Hazardous Air Pollutants (HAPs)

Other Classes -> Aromatic Ketones

Flammable agents - 2nd degree

Log Kow = 0.20

0.20

0.2

0.3

PENETRATING ODOR RESEMBLING THAT OF CHLORINE

Acrid, chlorine-like odor.

1.318 at 68 °F (USCG, 1999) - Denser than water; will sink

1.318 AT 20 °C/4 °C

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.0

1.318 @ 20°C

1.32

YELLOW MONOCLINIC PRISMS FROM WATER OR PETROLEUM ETHER

Greenish-yellowish solid

Pale-yellow solid.

Slightly soluble (NTP, 1992)

SOL IN ALKALIES, HOT PETROLEUM ETHER

> 10% in ether

> 10% in ethanol

Water solubility = 1.113X10+4 mg/l @ 18 °C

11.1 mg/mL at 18 °C

559 °F (NTP, 1992)

93 °C

100-200 °F (38-93 °C) (CLOSED CUP)

38-93 °C

100-200 °F

SUBLIMES (NTP, 1992)

~180 °C

Sublimes

240.3 °F (NTP, 1992)

115.7 °C

Heat of fusion at melting point = 1.845X10+7 J/kmol

115.7 °C

116 °C

115 °C

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301+H331 (14.8%): Toxic if swallowed or if inhaled [Danger Acute toxicity, oral; acute toxicity, inhalation]

P203, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Chemical: 2,5-Cyclohexadiene-1,4-dione

Hazard Traits - Dermatotoxicity

2,5-Cyclohexadiene-1,4-dione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,5-Cyclohexadiene-1,4-dione are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 14-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/24947

1,4-Benzoquinone: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Special Hazards of Combustion Products: Contain irritating and toxic fumes, including carbon dioxide and carbon monoxide.

· Combustible material: may burn but does not ignite readily.

Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 38 °C explosive vapour/air mixtures may be formed. Finely dispersed particles form explosive mixtures in air.

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. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Occupational exposure to quinone may occur in the dye, textile, chemical, tanning, and cosmetic industries. Acute (short-term) exposure to high levels of quinone, via inhalation in humans, results in irritation of the eyes, consisting of discoloration of the conjunctiva and cornea, and causes dermatitis from dermal exposure. Chronic (long-term) inhalation exposure to quinone in humans may result in visual disturbances, and chronic dermal contact causes skin ulceration. No information is available on the reproductive, developmental, or carcinogenic effects of quinone in humans. The results of available animal studies are insufficient to evaluate the carcinogenicity of quinone. EPA has not evaluated quinone for carcinogenicity.

Benzoquinone can cause skin necrosis after prolonged contact. A dermal sensitizer (DSEN); [ACGIH TLVs and BEIs] A skin, eye, and respiratory tract irritant; [ICSC] Can cause corneal ulcers after acute exposure and corneal opacities after chronic exposure; [CAMEO] Suspected germ cell mutagen (3B); [MAK]

2587 153

2587 153

U197; As stipulated in 40 CFR 261.33, when 1,4-benzoquinone, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Half-upright position. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give a slurry of activated charcoal in water to drink. Do NOT induce vomiting. Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

(General first aid procedures)

Extinguishant: Water spray, dry chemical, carbon dioxide.

/Wear a/ self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive pressure mode.

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources. /Benzoquinone/

1) VENTILATE AREA OF SPILL. 2) FOR SMALL QUANTITIES, SWEEP ONTO PAPER OR OTHER SUITABLE MATERIAL, PLACE IN APPROPRIATE CONTAINER & BURN IN SAFE PLACE (SUCH AS FUME HOOD). LARGE QUANTITIES MAY BE RECLAIMED; HOWEVER, IF ... NOT PRACTICAL, DISSOLVE IN FLAMMABLE SOLVENT (SUCH AS ALCOHOL) & ATOMIZE IN SUITABLE COMBUSTION CHAMBER EQUIPPED WITH APPROPRIATE EFFLUENT GAS CLEANING DEVICE.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U197, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

Biodegradation: Diluted waste waters may be purified by biological means with specially adjusted activated sludge. Biodegradation is greatly facilitated if the quinone wastes are reduced to hydroquinone prior to discharge. Suitable reducing agents are sodium sulfite and sulfur dioxide. Concentrated wastes are disposed of in special waste incinerators, whereby attention has to be given to the fact that quinone sublimes. Recommendable methods: Incineration, landfill, discharge to sewer. Peer-review: Dissolve in a suitable solvent before combustion. Small amt: landfill or well dilute and discharge to sewer. (Peer-review conclusions of an IRPTC expert consultation (May 1985))

A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

The worker should immediately wash the skin when it becomes contaminated.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

For more Preventive Measures (Complete) data for 1,4-BENZOQUINONE (11 total), please visit the HSDB record page.

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

THE INFLUENCE OF P-BENZOQUINONE ON POTASSIUM UPTAKE BY EXCISED SUGAR BEET & WHEAT ROOTS WAS STUDIED. WHEN P-BENZOQUINONE WAS ADDED TO NUTRIENT SOLUTION, IT ENHANCED ABSORPTION RATES OF BOTH SPECIES AT VERY LOW CONCN WHILE INHIBITION OCCURRED FOR HIGHER CONCN.

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

TERRESTRIAL FATE: 1,4-Benzoquinone was degraded very fast in a chernozem soil (persistence time not reported) leaving soil-stable metabolite residues(1); the fate processes by which the 1,4-benzoquinone was degraded in this chernozem soil were not reported(SRC). Based on a log Kow value of 0.20(2), 1,4-benzoquinone should have high mobility in soil(SRC) based on a suggested classification scheme(3). 1,4-Benzoquinone on soil surfaces may be susceptible to volatilization based on a Henry's Law constant of 4.79X10-4 atm-cu m/mol(SRC) calculated from a water solubility of 1.113X10+4 mg/l(4) and a vapor pressure of 37.5 mm Hg(5). 1,4-Benzoquinone on soil surfaces may also be susceptible to photodegradation(6,7,SRC).

AQUATIC FATE: 1,4-Benzoquinone released to the aquatic environment is not expected to significantly volatilize(SRC) based on a Henry's Law constant of 4.79X10-4 atm-cu m/mol(SRC) calculated from a water solubility of 1.113X10+4 mg/l(1) and a vapor pressure of 37.5 mm Hg(2). Adsorption to suspended solids and sediment should also not be important based upon the high water solubility of 1,4-benzoquinone(SRC). An estimated BCF value of 0.84(3,SRC), from an experimental Kow of 0.20(4), suggests that 1,4-benzoquinone will not bioaccumulate in aquatic organisms(SRC) according to a recommended classification scheme(5). Since it absorbs UV radiation in environmentally significant wavelengths(6,7), direct photolysis is possible(SRC). Sufficient data are not available to predict the significance of biodegradation but its rapid loss in soil suggests that biodegradation may be important(SRC).

ATMOSPHERIC FATE: According to a suggested classification scheme(1), a vapor pressure of 37.5 mm Hg at 25 °C(2) indicates that 1,4-benzoquinone will exist in the vapor phase in the ambient atmosphere. Vapor phase 1,4-benzoquinone is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals and ozone(SRC); the combined half-life for this reaction in air is estimated to be about 33.6 minutes(3,SRC). Since it absorbs UV radiation in environmentally significant wavelengths(4,5), photolysis is also possible(SRC).

The substance can be absorbed into the body by inhalation and by ingestion.

inhalation, ingestion, skin and/or eye contact

Quinone is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Burning sensation. Cough. Laboured breathing. Shortness of breath. Sore throat.

Redness. Pain. Skin discoloration. Blisters.

Redness. Pain. Blurred vision. Brown staining.

Abdominal pain. Burning sensation. Diarrhoea. Vomiting.

Eye irritation, conjunctivitis; keratitis (inflammation of the cornea); skin irritation

Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.

Careful examination of eyes, incl visual acuity & slit lamp examinations, should be done during placement & periodic examinations. Also evaluate skin.

Carry out medical examination for the workers every year, especially on eyes and skin. Workers must be /protected/ against eye and skin irritation.

U197; As stipulated in 40 CFR 261.33, when 1,4-benzoquinone, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,4-Benzoquinone is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. 1,4-Benzoquinone is produced, as an intermediate or final product, by process units covered under this subpart.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Quinone is included on this list.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.45 kg. The toll free telephone number of the NRC is (800) 424-8802; In the Washington metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.6 (section IV. D.3.b).

IN PIG PARA-QUINONE IS METABOLIZED TO P-BENZOSEMIQUINONE & QUINOL. /FROM TABLE/

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/

Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure.

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)

Quinone is used as a chemical intermediate, a polymerization inhibitor, an oxidizing agent, a photographic chemical, a tanning agent, and a chemical reagent.

Used in the production of hydroquinone, dyes, and fungicides; also used as an oxidizing agent and photographic chemical; [ACGIH]

Photographic Processing [Category: Other]

TANNING HIDES; MAKING GELATIN INSOL; STRENGTHENING ANIMAL FIBERS

FOR P-BENZOQUINONEDIOXIME, A RUBBER ACCELERATOR, FOR QUINHYDRONE USED IN PH ELECTRODES, FOR 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE; CHEM INTERMEDIATE FOR DYES-EG, VAT YELLOW 5 (FORMER USE)

USED IN COSMETIC INDUSTRIES PRIMARILY BECAUSE OF ITS ABILITY TO TRANSFORM CERTAIN NITROGEN-CONTAINING CMPD INTO VARIETY OF COLORED SUBSTANCES

2023: 19,841 lb

(1977) AT LEAST 4.59X10+7 G

(1982) PROBABLY GREATER THAN 2.27X10+6 G

QUINONE CAN BE PREPD ... BY THE REDUCTION OF HYDROQUINONE WITH BROMIC ACID.

OXIDATION OF ANILINE WITH MANGANESE DIOXIDE & SULFURIC ACID

/1,4-Benzoquinone is prepd/ by the oxidation of aniline with chromic acid, extraction with ether and distillation.

PARA-QUINONE IS AVAILABLE IN USA AS TECHNICAL GRADE ... GRADE AVAILABLE IN JAPAN HAS PURITY OF OVER 99%.

/Available/ ... in assay 98% grades.

All Other Chemical Product and Preparation Manufacturing

2,5-Cyclohexadiene-1,4-dione: ACTIVE

1,4-Benzoquinone reacts with trialkylboranes to produce alkyl substituted hydroquinones