PHENOLS AND PHENOLIC COMPOUNDS

 

 

Phenols are derivatives of benzene and have a hydroxyl group (-OH) attached to the benzene ring.

 

Uses

Phenols find use in industry as antioxidants, chemical intermediates, disinfectants, tanning agents, photographic developers, and additives to lubricants and gasoline. They are widely used in the photography, petroleum, paint, explosive, rubber, plastics, pharmaceutical and agricultural industries. The three major uses for phenols are found in the manufacture of phenolic resins, bisphenol A and caprolactam.

 

Phenol is used in the manufacture of a variety of compounds, including drugs, dyes and colourless or light-coloured artificial resins. It is a general disinfectant for toilets, stables, cesspools, floors and drains, as well as an extractive solvent for petroleum refining. Phenol is found in germicidal paints, slimicides and glue. Catechol is used particularly as an antioxidant in the rubber, chemical, photography, dye, fat and oil industries. It is also employed in cosmetics and in some pharmaceuticals.

 

Resorcinol is used in the tanning, cosmetics, rubber, pharmaceutical and photography industries, and in the manufacture of explosives, dyes, organic chemicals and antiseptics. It is found in adhesives for tyres, rubber and wood. Resorcinol is also an indirect food additive polymer for use as a basic component of single and repeated use food contact surfaces. Hydroquinone is a reducing agent and is used extensively as a photographic developer, an antioxidant, and a stabilizer in paints, varnishes, motor fuels and oils. Many derivatives of hydroquinone have been used as bacteriostatic agents. Pyrogallic acid also serves as a developer in photography as well as a mordant for wool, a dyeing agent for furs and hair, an antioxidant in lubricating oils, and a reducing agent for gold, silver and mercury salts. It is used for staining leather, preparing synthetic drugs, and for maintaining anaerobic conditions for bacterial growth. Its use is based primarily on its property of being easily oxidized in alkaline solutions (even by atmospheric oxygen).

 

2,4-Dimethyl phenol is used to manufacture pharmaceuticals, plastics, insecticides, fungicides, rubber chemicals, wetting agents and dye-stuffs. It acts as a solvent, disinfectant, germicide and sanitizer in commercial mixtures used in all hospital areas, instruments and equipment. o-Phenyl phenol has numerous functions as a fungicide, germicide and household disinfectant. It is used in the rubber and food-storage industries and serves as a dye-stuff carrier for polyester fibres and a disinfectant for cutting oils, timber and paper.

 

The cresols have wide applications in the phenolic resin, explosive, petroleum, photographic, paint and agricultural industries. They are ingredients of many household disinfecting solutions. Cresol is also an additive to lubricating oils and a component of degreasing compounds and paintbrush cleaners. m-Cresol is a textile scouring agent; o-cresol is used in tanning, fibre treatment and metal degreasing; p-cresol is a solvent for wire enamels and an agent used in metal cleaning, ore flotation, synthetic flavouring and perfumes.

 

The chlorophenols are intermediates in the synthesis of dyes, pigments and phenolic resins. Certain chlorophenols are used directly as mould inhibitors, antiseptics, disinfectants and anti-gumming agents for gasoline. Pentachlorophenol and its sodium salt are used to protect various industrial products from microbiological attack. These include wood and other cellulosic products, starches, adhesives, proteins, leather, finished yarn and cloth, photographic solutions, oils, paints, latex and rubber. Pentachlorophenol is used in the construction of boats and buildings, for mould control in petroleum drilling and production, and as an antibacterial agent in disinfectants and cleaners. It is also useful in the treatment of cable coverings, canvas belting, nets, poles and cooling-tower water. Pentachlorophenol is equally important in controlling termites in wood and insulating board, powder post beetles and other wood-boring insects, and slime and algae. It is also used in manufacturing herbicides, and as an agent to inhibit fermentation in various materials.

 

Some chlorophenols are used as intermediates and preservatives in the paint, textile, cosmetics and leather industries. 2-Chlorophenol and 2,4-dichlorophenol are used in organic synthesis. 2-Chlorophenol is utilized in the manufacture of dye-stuffs and in the process for extracting sulphur and nitrogen compounds from coal. 2,4,5-Trichlorophenol is a preservative for adhesives, synthetic textiles, rubber, wood, paints and paper; and 2,4,6-trichlorophenol is a wood and glue preservative. The tetrachlorophenols (and their sodium salts) have been used as fungicides and wood preservatives.

 

Hazards

 

Phenol

Phenol is readily absorbed through the skin and from the gastroenteric tract, while phenol vapours are readily absorbed into the pulmonary circulation. After absorption of a sublethal dose, most of the phenol is oxidized or conjugated with sulphuric, glucuronic and other acids, and excreted with the urine as “conjugated” phenol. A small portion is excreted as “free” phenol. The toxic effects of phenol are related directly to the concentration of free phenol in the blood.

 

In humans, acute phenol poisoning results in vasodilation, cardiac depression, hypothermia, coma and respiratiory arrest. Ingested phenol causes intense abdominal pain, and mouth burning occurs. Acute renal failure may also result. In animals, the signs of an acute intoxication are very similar, regardless of the site or the mode of administration of this compound. The predominant effects are exerted upon the motor centres in the spinal cord, resulting in tremors and severe convulsions. Chronic phenol poisoning is reported comparatively infrequently today. Severe cases are characterized by systemic disorders such as digestive disturbances, including vomiting, difficulty in swallowing, ptyalism, diarrhoea and anorexia; by nervous disorders, with headache, fainting, vertigo and mental disturbances; and possibly by ochronosis and an eruption on the skin. The prognosis is grave when there is extensive damage to the liver and kidneys. Ingestion of a dose of 1 g of phenol has been lethal to humans. Approximately every second reported case of acute phenol poisoning has resulted in death.

 

Generally speaking, the signs and symptoms of intoxication by di- and trihydroxy phenols  (resorcinol, hydroquinone, pyrogallol) resemble that of phenol toxicity. The antipyretic action of resorcinol is more marked than that of phenol. The cutaneous application of solutions or salves containing 3 to 5% of resorcinol has resulted in local hyperaemia, itching dermatitis, oedema and loss of the superficial layers of the skin. The approximate lethal dose of resorcinol, in aqueous solution, for rabbits is 0.75 g/kg, and for rats and guinea-pigs, 0.37 g/kg. Hydroquinone is more toxic than phenol. Lethal doses have been reported as 0.2 g/kg (rabbit) and 0.08 g/kg (cat). Skin breakdown and irritation has been reported with dermal application of pyrogallol. Eventually with repeated contact, skin sensitization can occur. The symptoms observed in acute intoxications in humans resemble closely the signs displayed by experimental animals. These may include vomiting, hypothermia, fine tremors, weakness, muscular incoordination, diarrhoea, loss of reflexes, coma, asphyxia, and death by respiratory failure. Estimated lethal doses of aqueous pyrogallol are 1.1 g/kg (orally) for the rabbit,  0.35 g/kg (subcutaneously) for a cat or dog , and 0.09 g/kg (intravenously) in dogs.

 

Pentachlorophenol and its sodium salt are capable of inducing discomfort and local or systemic effects. Skin irritation is likely to result from a relatively brief, single exposure to a solution containing approximately 10% of the material. A 1% solution may cause irritation if contact is repeated. A solution containing 0.1% or less may result in adverse effects after prolonged contact. The symptoms of severe systemic intoxication include loss of appetite, respiratory difficulties, anaesthesia, hyperpyrexia, sweating, dyspnoea and a rapidly progressive coma.

 

Fine dusts and sprays of pentachlorophenol or sodium pentachlorophenate will cause painful irritation to the eyes and upper respiratory tract, respiratory tract and the nose. Atmospheric concentrations appreciably greater than 1  of air will cause this pain in the uninitiated person. Pentachlorophenol is classified by IARC as a Group 2B possible human carcinogen.

 

Other chlorophenols. Dermatoses in humans caused by tetrachlorophenol and its sodium salt have been reported; these included papulofollicular lesions, sebaceous cysts and marked hyperkeratosis. Occupational exposure to chlorophenols increases the risk of soft-tissue sarcomas. Chlorophenoxy derivatives including 2,4-dichlorophenoxyacetic acid, 2,4,5-trichlorophenoxyacetic acid, 2,4,5-trichlorophenoxypropionic acid, and 2,4-D salts and esters are discussed elsewhere in this chapter and Encyclopaedia.

 

Signs of intoxication due to o-, m- and p-chlorophenol in rats include restlessness, increased rate of respiration, rapidly developing motor weakness, tremors, clonic convulsions, dyspnoea and coma. The 2,4- and 2,6-dichlorophenols and 2,4,6- and 2,4,5-trichlorophenols also produce these signs, but decreased activity and motor weakness do not appear quite so promptly. The tremors are much less severe, but, in this case also, they continue until a few minutes before death. Tetrachlorophenols take an intermediate place between the lower homologues and pentachlorophenol. These compounds also produce signs similar to those caused by the mono-, di- and trichlorophenols; however, they do not as a rule cause hyperpyrexia.

 

Dermatoses, including photoallergic contact dermatitis, have been reported in humans after exposure to 2,4,5-trichlorophenol, chloro-2-phenylphenol and tetrachlorophenols; these included papulofollicular lesions, comedones, sebaceous cysts and marked hyperkeratosis (chloracne).

 

Bromo- and iodophenols. The bromo- and iodophenols are rapidly absorbed from the gastroenteric tract. The approximate lethal oral dose of pentabromophenol is 200 mg/kg rat; of 2,4,6-tribromophenol, 2.0 g/kg rat; and of 2,4,6-triiodophenol, from 2.0 to 2.5 g/kg rat. In rats and guinea-pigs the subcutaneous  of o-bromophenol are 1.5 and 1.8 g/kg, respectively. Generally, the symptoms are similar to those of pentachlorophenol. Pentabromophenol also caused tremors and convulsions.

 

On the basis of the results of animal experiments, the halogenated phenols, pentabromophenol and sodium and copper pentachlorophenate are considered safe for use as molluscicides in the field, if reasonable precautions are taken in their application.

 

Catechol (pyrocatechol). Contact with the skin has been known to cause an eczematous dermatitis, while in a few instances absorption through the skin has resulted in symptoms of illness closely resembling those induced by phenol, with the exception of certain marked central effects (convulsions). Toxic or lethal doses induced phenol-like signs of illness in experimental animals. However, unlike phenol, large doses of pyrocatechol cause a predominant depression of the central nervous system and a prolonged rise of blood pressure. The rise of blood pressure appears to be due to peripheral vasoconstriction.

 

The repeated absorption of sublethal doses by animals has induced methaemoglobinaemia, leucopenia and anaemia. Death is apparently initiated by respiratory failure.

 

Pyrocatechol is more acutely toxic than phenol. The approximate lethal oral dose is 0.3 g/kg for the dog, and 0.16 g/kg for the guinea-pig. Pyrocatechol is readily absorbed from the gastroenteric tract and through the intact skin. After absorption, part of the catechol is oxidized with polyphenol oxidase to o-benzoquinone. Another fraction conjugates in the body with hexuronic, sulphuric and other acids, while a small amount is excreted in the urine as free pyrocatechol. The conjugated fraction hydrolyzes in the urine with the liberation of the free compound; this is oxidized with the formation of dark-coloured substances which are responsible for the smoky appearance of the urine. Apparently, pyrocatechol acts by mechanisms similar to those reported for phenol.

 

Quinone. Large doses of quinone which have been absorbed from the subcutaneous tissues or from the gastroenteric tract of animals, induce local changes, crying, clonic convulsions, respiratory difficulties, drop in blood pressure and death by paralysis of the medullary centres. Asphyxia appears to play a major role in causing death because of pulmonary damage resulting from excretion of quinone into the alveoli and because of certain not too well defined effects of quinone upon haemoglobin. The urine of severely poisoned animals may contain protein, blood, casts, and free and conjugated hydroquinone.

 

In humans, severe local damage to the skin and mucous membranes may follow contact with the crystalline material, solutions of quinone and quinone vapour condensing upon exposed parts of the body (particularly moist surfaces). Local changes may include discolouration, severe irritation with erythema, swelling, and the formation of papules and vesicles. Prolonged skin contact may lead to necrosis. Vapours condensing upon the eyes are capable of inducing serious disturbances of vision. It was reported that the injury usually extends through the entire layer of the conjunctiva and is characterized by a deposit of pigment. The staining, varying from diffuse brown to globules of brownish-black, is located primarily in the zones extending from the canthi medially to the edges of the cornea. All layers of the cornea are involved in the injury, with a resultant discolouration that may be white and opaque or brownish-green and translucent. Alteration of the cornea can occur after the pigment has disappeared. Ulceration of the cornea has resulted from one brief exposure to a high concentration of the vapour of quinone, as well as from repeated exposures to moderately high concentrations.

 

Cresols and derivatives. Pure cresol is a mixture of ortho- (o-), meta- (m-) and para (p-) isomers, while cresylic acid, sometimes used synonymously for a mixture of cresols, is defined as a mixture of cresols, xylenols and phenol in which 50% of the material boils above 204°C. The relative concentration of the isomers in pure cresol is determined by the source. The toxic effects of cresol are similar to those of phenol. It can be absorbed through the skin, from the respiratory system, and from the digestive system. The rate of penetration through the skin is more dependent upon the surface area than on the concentration.

 

Like phenol, it is a general protoplasmic poison and is toxic to all cells. Concentrated solutions are locally corrosive to the skin and mucous membranes, while dilute solutions cause redness, vesiculation and ulceration of the skin. Skin contact has also resulted in facial peripheral neuritis, impairment of renal function, and even necrosis of liver and kidneys. A sensitivity dermatitis may occur in susceptible people from solutions of less than 0.1%. Systemically, it is a severe depressant of the cardiovascular and central nervous systems, particularly the spinal cord and medulla. Oral administration causes a burning sensation in the mouth and oesophagus, and vomiting may result. Concentrations of vapour that can be produced at relatively high temperatures may cause irritation of the upper airways and nasal mucosa. Systemic absorption is followed by vascular collapse, shock, low body temperature, unconsciousness, respiratory failure and death. Pancreatic complications have been described. The oral toxic dose for small animals averages about 1 mg/kg, and specifically 0.6 mg/kg for p-cresol, 0.9 mg/kg for o-, and 1.0 mg/kg for m-cresol. On the basis of its similarity to phenol, the human fatal dose can be estimated to be about 10 g. In the body, some of it is oxidized to hydroquinone and pyrocatechin, and the remainder and largest proportion is excreted unchanged, or conjugated with glycuronic and sulphuric acids. If urine is passed, it contains blood cells, casts and albumin. Cresol is also a moderate fire hazard.

 

Safety and Health Measures

These substances must be handled with caution. Inhalation of the vapours, and dust and skin contact with solutions of these materials, must be avoided to prevent local effects and absorption. The ingestion even of traces should be prevented. If exposure to the dust cannot be completely avoided, the nose and mouth should be protected with a respirator or folded gauze, and the eyes with tight-fitting goggles. Protective clothing, including rubber (not cotton) gloves, should be worn. Clothing should be removed immediately if contaminated by spillage. All clothing worn during one spraying operation should be laundered before re-use. Routine precautions include washing hands, arms, and face with soap and water before eating, drinking or smoking. At the end of each day, a worker should shower and change into clean clothing.

 

Measures that apply to phenol and its derivatives include:

 

· careful instruction of persons engaged in the manufacture, handling, storage and transport of phenol

· effective ventilation

· proper disposal of phenolic wastes with precautions against the possible pollution of air, streams and underground waters, since aquatic species are particularly susceptible to the effects of chemicals in this family

· special precautions in tank cleaning, which should not be attempted without proper gear, forced-air supply, a rescue harness and lifeline, hose mask, boots, rubber apron and gloves, and a “watcher” stationed at the entrance of the tank

· continuous vigilance on the part of the hygienist or physician for signs and symptoms of acute or chronic (local or systemic) intoxication

· fire prevention precautions.

 

First aid. In the event of an acute exposure, speed in treatment is essential. The offending agent must be removed from the skin, which is done most efficiently by flooding the affected area with water. After several minutes under the shower, continue decontamination with repeated swabbings or sprayings with polyethyleneglycol-300 until the danger of collapse has passed. If the exposed area is covered by clothing, remove it under the shower. Cover phenol burns lightly with a clean, white cloth. Do not use greases, powders or ointments in the first-aid treatment of such burns. Hospital treatment may include sedation, removal of dead tissue, fluid therapy, and the administration of antibiotics and vitamins. If phenol is splashed into eyes, copious irrigation with water for at least 15 minutes is necessary. All but the most trivial eye injuries should be referred to an ophthalmologist.

 

Speed is equally essential if a phenol has been ingested. Appropriate first aid must be available, and local medical facilities must be completely informed of the possibility of accidents and be prepared for emergency medical treatment. The treatment of chronic phenol poisoning is symptomatic after the individual has been removed from the site of exposure.

 

Phenols and phenolic compounds tables

Table 104.137 - Chemical information.

Table 104.138 - Health hazards.

Table 104.139 - Physical and chemical hazards.

Table 104.140 - Physical and chemical properties.

 

___________________________________________________________________________

 

Table 104.137      Phenols & Phenolic Compounds: Chemical identification

 

CHEMICAL

SYNONYMS/ UN CODE

CAS-number

CHEMICAL FORMULA

2,6-DI-tert-BUTYL-p-CRESOL

2,6-Bis(1,1-dimethylethyl)-4-methylphenol;

Butylated hydroxytoluene;

Butylhydroxytoluene;

DBMP;

DBPC;

2,6-Di-tert-butyl-1-hydroxy-4-methylbenzene;

3,5-Di-tert-butyl-4-hydroxytoluene;

2,6-Di-tert-butyl-p-methylphenol;

2,6-Di-tert-butyl-4-methylphenol;

4-Hydroxy-3,5-di-tert-butyltoluene

128-37-0

 

 

2,6-DI-tert-BUTYLPHENOL

2,6-Bis(tert-butyl)phenol

128-39-2

 

 

p-tert-BUTYLPHENOL

4-tert-Butylphenol;

4-(1,1-Dimethylethyl)phenol;

1-Hydroxy-4-tert-butylbenzene;

Phenol, 4-(1,1-Dimethylethyl)-;

PTBP

98-54-4

 

 

4-tert-BUTYL PYROCATECHOL

1,2-Benzenediol, 4-(1,1-Dimethylethyl)-;

4-tert-butyl-1,2-benzenediol;

4-tert-Butylcatechol;

p-tert-Butylpyrocatechol;

4-tert-Butylpyrocatechol

98-29-3

 

 

CATECHOL

o-Benzenediol;

1,2-Benzenediol;

Catechol;

o-Dihydroxybenzene;

1,2-Dihydroxybenzene;

o-Dioxybenzene;

o-Diphenol;

o-Hydroquinone;

o-Hydroxyphenol;

2-Hydroxyphenol;

o-Phenylenediol

120-80-9

 

 

p-CHLORO-m-CRESOL

4-Chlor-m-cresol;

Chlorocresol;

p-Chlorocresol;

6-Chloro-m-cresol;

2-Chloro-hydroxytoluene

59-50-7

 

 

o-CHLOROPHENOL

2-Chlorophenol

95-57-8

 

 

m-CHLOROPHENOL

3-Chlorophenol

108-43-0

 

 

p-CHLOROPHENOL

4-Chlorophenol

106-48-9

 

 

o-CRESOL

2-Cresol;

o-Cresylic acid;

1-Hydroxy-2-methylbenzene;

o-Hydroxytoluene;

2-Hydroxytoluene;

o-Methylphenol;

2-Methylphenol;

o-Methylphenylol;

o-Oxytoluene;

Phenol

UN2076

95-48-7

 

 

m-CRESOL

3-Cresol;

m-Cresylic acid;

1-Hydroxy-3-methylbenzene;

m-Hydroxytoluene;

3-Hydroxytoluene;

m-Methylphenol;

3-Methylphenol

UN2076

108-39-4

 

 

p-CRESOL

4-Cresol;

p-Cresylic acid;

1-Hydroxy-4-methylbenzene;

p-Hydroxytoluene;

4-Hydroxytoluene;

p-Methylhydroxybenzene;

1-Methyl-4-hydroxybenzene;

p-Methylphenol;

4-Methylphenol

UN2076

106-44-5

 

 

CRESOL, ALL ISOMERS

Cresylic acid;

Cresylic acid;

Methylphenol;

Tekresol;

Ar-toluenol;

Tricresol

UN2022

1319-77-3

 

 

2,4-DICHLOROPHENOL

2,4-DCP;

2,4-Dichlorohydroxybenzene

120-83-2

 

 

2,5-DICHLOROPHENOL

 

583-78-8

 

 

3,5-DICHLOROPHENOL

 

591-35-5

 

 

2,4-DIMETHYLPHENOL

4,6-Dimethylphenol;

1-Hydroxy-2,4-Dimethylbenzene;

m-Xylenol;

2,4-Xylenol

105-67-9

 

 

DINITRO-o-CRESOL

Dinitrocresol;

2,4-Dinitro-o-cresol;

4,6-Dinitro-o-cresol;

Dinitrodendtroxal;

3,5-Dinitro-2-hydroxytoluene;

Dinitrol;

Dinitromethyl cyclohexyltrienol;

2,4-Dinitro-6-methylphenol;

DNOC;

2-Methyl-4,6-dinitrophenol;

Nitrador

UN1598

534-52-1

 

 

HYDROQUINONE

p-Benzenediol;

1,4-Benzenediol;

Benzohydroquinone;

Benzoquinol;

Dihydroxybenzene;

p-Dihydroxybenzene;

1,4-Dihydroxybenzene;

p-dioxobenzene;

p-Dioxybenzene;

p-Hydroquinone

UN2662

123-31-9

 

 

2-HYDROXYBIPHENYL

o-Biphenylol;

2-Biphenylol;

o-Diphenylol;

o-Hydroxydiphenyl;

2-Hydroxydiphenyl;

Orthohydroxydiphenyl

90-43-7

 

 

4-METHOXYPHENOL

Hydroquinone monomethyl ether;

p-Methoxyphenol;

4-Methoxyphenol;

MME;

Monomethyl ether hydroquinone

150-76-5

 

 

NONYL PHENOL, ALL ISOMERS

Hydroxyl no. 253

25154-52-3

 

 

PENTACHLOROPHENOL

Dowcide 7;

Dow pentachlorophenol DP-2 antimicrobial;

Durotox;

EP 30;

1-Hydroxypentachlorobenzene;

Lauxtol;

Lauxtol A;

Liroprem

87-86-5

 

 

PHENOL

Benzenol;

Carbolic acid;

Hydroxybenzene;

Monohydroxybenzene;

Monophenol;

Oxybenzene;

Phenic acid;

Phenol alcohol;

Phenyl hydrate;

Phenyl hydroxide;

Phenylic acid;

Phenylic alcohol

UN1671

UN2312

UN2821

108-95-2

 

 

PENTACHLOROPHENOL, SODIUM SALT

Pentachlorophenate sodium;

Pentachlorophenoxy sodium;

Pentaphenate;

Sodium pentachlorophenate;

Sodium pentachlorophenol;

UN2567

131-52-2

 

 

PYROGALLOL

Benzene, 1,2,3-trihydroxy-;

1,2,3-Benzenetriol;

Fouramine Brown AP;

Fourrine PG;

Fourrine 85;

Pyrogallic acid;

1,2,3-Trihydroxybenzene

87-66-1

 

 

RESORCINOL

m-Benzenediol;

1,3-Benzenediol;

m-Dihydroxybenzene;

1,3-Dihydroxybenzene;

m-Dioxybenzene;

m-Hydroquinone;

3-Hydroxycyclohexadien-1-one;

m-Hydroxyphenol;

3-Hydroxyphenol;

Phenol, m-hydroxy-

UN2876

108-46-3

 

 

2,3,5,6-TETRACHLOROPHENOL

 

935-95-5

 

 

2,4,5,6-TETRACHLOROPHENOL

Dowicide 6;

TCP;

2,3,4,6-Tetrachlorophenol

58-90-2

 

 

4,4’-THIOBIS(6-tert-BUTYL-m-CRESOL)

Bis(3-tert-butyl-4-hydroxy-6-methylphenyl) sulphide;

Bis(4-hydroxy-5-tert-butyl-2-methylphenyl) sulphide;

4,4’-Thiobis(6-tert-butyl-m-cresol)

96-69-5

 

 

2,3,4-TRICHLOROPHENOL

 

15950-66-0

 

 

2,3,5-TRICHLOROPHENOL

 

933-78-8

 

 

2,4,6-TRICHLOROPHENOL

 

88-06-2

 

 

2,4,5-TRICHLOROPHENOL

Collunosol;

Dowcide 2;

Dowicide 2;

Dowicide B;

Nurelle;

Preventol I

95-95-4

 

 

2,3,6-TRICHLORO PHENOL

 

933-75-5

 

 

XYLENOL

Dimethylphenol;

Phenol, dimethyl-

UN2261

1300-71-6

 

 

___________________________________________________________________________

 

Table 104.138      Phenols & Phenolic Compounds: Health hazards

 

CHEMICAL NAME

CAS-NUMBER

ICSC SHORT-TERM EXPOSURE

ICSC LONG-TERM EXPOSURE

ICSC ROUTES OF EXPOSURE AND SYMPTOMS

US NIOSH TARGET ORGANS & ROUTES OF ENTRY

US NIOSH SYMPTOMS

CATECHOL

120-80-9

eyes; skin; resp tract; GI tracts; CNS; blood

skin

Inhalation: cough, laboured breathing

Skin: may be absorbed, redness

Eyes: redness, severe deep burns

Ingestion: abdominal pain, diarrhoea, vomiting,

Eyes; skin; resp sys; CNS; kidneys

Inh; abs; ing; con

Irrit eyes, skin, resp sys; skin sens, derm; lac, burned eyes; convuls, incr BP, kidney inj

p-CHLOROPHENOL

106-48-9

eyes; skin; resp. tract; CNS; bladder

liver; lungs; kidneys; blood; heart

Inhalation: cough, dizziness, headache, laboured breathing, sore throat

Skin: may be absorbed, redness

Eyes: redness

Ingestion: abdominal pain

 

 

o-CRESOL

95-48-7

eyes; skin; resp tract; lungs; CNS

skin; lungs; liver; kidneys

Inhalation: burning sensation, cough, headache, laboured breathing, nausea, vomiting

Skin: may be absorbed, redness, pain, blisters

Eyes: redness, pain, severe deep burns

Ingestion: abdominal cramps, burning sensation, collapse

Eyes, skin, resp sys, CNS, liver, kidneys, pancreas, CVS

Inh; abs; ing; con

Irrit eyes, skin, muc memb; CNS effects: conf, depres, resp fail; dysp, irreg rapid resp, weak pulse; eye, skin burns; derm; lung, liver, kidney, pancreas damage

m-CRESOL

108-39-4

CNS

skin; lungs; liver; kidneys; CNS

Inhalation: cough, headache, laboured breathing, nausea, unconsciousness

Skin: may be absorbed, roughness

Eyes: severe deep burns

Ingestion: dizziness, dullness, headache, unconsciousness

Eyes; skin; resp sys; CNS; liver; kidneys; CVS; pancreas

Inh; abs; ing; con

Irrit eyes, skin, muc memb; CNS effects: conf, depres, resp fail; dysp, irreg rapid resp, weak pulse; eye, skin burns; derm; lung, liver, kidney, pancreas damage

p-CRESOL

106-44-5

eyes; skin; resp tract; lungs; CNS

skin; lungs; liver; kidneys

Inhalation: burning sensation, cough, headache, laboured breathing, nausea, vomiting

Skin: may be absorbed, redness, pain, blisters

Eyes: redness, pain, severe deep burns

Ingestion: abdominal cramps, burning sensation, collapse

Eyes, skin; resp sys; CNS; liver; kidneys; pancreas; CVS

Inh; abs; ing; con

Irrit eyes, skin, muc memb; CNS effects: conf, depres, resp fail; dysp, irreg rapid resp, weak pulse; eye, skin burns; derm; lung, liver, kidney, pancreas damage

CRESOL, ALL ISOMERS

1319-77-3

eyes; skin; resp tract; lungs; CNS

skin; lungs; kidneys; liver

Inhalation: confusion, cough, dizziness, headache, shortness of breath, sore throat, unconsciousness, weakness, US NIOSH Symptoms may be delayed

Skin: may cause toxic effects within 20-30 minutes after skin contact, may be absorbed, redness, serious skin burns, pain

Eyes: irritation, pain, severe deep burns

Ingestion: abdominal pain, diarrhoea, vomiting

 

 

2,6-DI-tert-BUTYL-p-CRESOL

128-37-0

eyes; skin; resp tract

skin

Inhalation: cough, sore throat

Skin: may be absorbed, redness, pain

Eyes: redness, pain

Ingestion: abdominal pain, diarrhoea, dizziness, headache, vomiting

Eyes, skin

Inh; ing; con

Irrit eyes, skin; in animals: decr growth rate, incr liver weight

2,4-DICHLOROPHENOL

120-83-2

 

 

Ingestion: dizziness, headache, convulsion, body temperature change

 

 

2,5-DICHLOROPHENOL

583-78-8

eyes; skin; resp. tract

 

Inhalation: see ingestion

Skin: may be absorbed, redness, skin burns, pain

Eyes: redness, pain, severe deep burns

Ingestion: abdominal pain, burning sensation, diarrhoea, dizziness, headache, laboured breathing, nausea, vomiting, weakness, loss of coordination

 

 

3,5-DICHLOROPHENOL

591-35-5

skin; eyes; resp. tract

 

Inhalation: see ingestion

Skin: may be absorbed, redness, skin burns, pain

Eyes: redness, pain

Ingestion: abdominal pain, burning sensation, diarrhoea, dizziness, headache, laboured breathing, nausea, vomiting, weakness, loss of coordination

 

 

DINITRO-o-CRESOL

534-52-1

 

 

 

CVS; endocrine sys; eyes

Inh; abs; ing; con

Sense of well being; head, fever, lass, profuse sweat, profuse thirst, tacar, hyperpnea, cough, short breath, coma

HYDROQUINONE

123-31-9

eyes; skin; resp tract

skin

Inhalation: cough, laboured breathing

Skin: redness

Eyes: redness, pain, blurred vision

Ingestion: blue skin, dizziness, headache, nausea, shortness of breath, convulsions, vomiting, ringing in the ears

Eyes; resp sys; skin; CNS

Inh; ing; con

Irrit eyes, conj, kera; CNS excitement; colored urine, nau, dizz, suffocation, rapid breath; musc twitch, delirium; collapse; skin irrit, sens, derm

2-HYDROXYBIPHENYL

90-43-7

eyes; skin; resp tract

 

Inhalation: see ingestion

Skin: redness

Eyes: redness

Ingestion: abdominal cramps, abdominal pain, cough, laboured breathing

 

 

NONYLPHENOL, ALL ISOMERS

25154-52-3

eyes; skin; resp tract; lungs

 

Inhalation: burning sensation, cough, laboured breathing, sore throat, unconsciousness

Skin: redness, skin burns, pain

Eyes: redness, pain, blurred vision

Ingestion: abdominal pain, diarrhoea, nausea, sore throat

 

 

PENTACHLOROPHENOL

87-86-5

eyes; skin; resp. tract; lungs; heart

skin; lungs; CNS liver; kidneys

Inhalation: cough, dizziness, drowsiness, headache, laboured breathing, sore throat

Skin: may be absorbed, redness, blisters

Eyes: redness, pain

Ingestion: abdominal cramps, diarrhoea, nausea, unconsciousness, vomiting, weakness

CVS; resp sys; eyes; liver; kidneys; skin; CNS

Inh; abs; ing; con

Irrit eyes, nose, throat; sneez, cough; weak, anor, low-wgt; sweat; head, dizz; nau, vomit; dysp, chest pain; high fever; derm

PENTACHLOROPHENOL, SODIUM SALT

131-52-2

eyes; skin; resp. tract; lungs

skin; CNS; lungs; liver; kidneys

Inhalation: cough, dizziness, drowsiness, headache, perspiration, laboured breathing, sore throat

Skin: may be absorbed, redness, skin burns, burning sensation

Eyes: redness, pain, loss of vision

Ingestion: fever, perspiration, excitement, convulsion, coma

 

 

PHENOL

108-95-2

eyes; skin; resp tract; lungs; CNS; liver; kidneys

skin; kidneys; liver

Inhalation: burning sensation, cough, dizziness, headache, nausea, shortness of breath, unconsciousness, vomiting, US NIOSH Symptoms may be delayed

Skin: may be absorbed, serious skin burns, shock, collapse, coma, convulsion, local anesthetic effect, death

Eyes: permanent loss of vision, severe deep burns

Ingestion: abdominal pain, convulsions, diarrhoea, shock or collapse, sore throat, smoky, greenish-dark urine,

Liver; kidneys; skin; eyes, resp sys

Inh; abs; ing; con

Irrit eyes, nose, throat; anor, low-wgt; weak, musc ache, pain; dark urine; cyan; liver, kidney damage; skin burns; derm; ochronosis; tremor, convuls, twitch

PYROGALLIC ACID

87-66-1

eyes; skin; resp tract; liver; kidneys; blood

skin

Inhalation: blue lips or finger nails, blue skin, cough, dizziness, headache, laboured breathing, nausea, shortness of breath, sore throat

Skin: may be absorbed, redness, pain, local discoloration

Eyes: redness, pain

Ingestion: abdominal pain, nausea, vomiting, weakness

 

 

2,3,5,6-TETRACHLOROPHENOL

935-95-5

 

 

Inhalation: cough, sore throat

Skin: may be absorbed, redness, pain

Eyes: redness, pain

Ingestion: abdominal pain, diarrhoea, dizziness, headache, nausea, fatigue, muscular spasms, increased body temperature and sweating

 

 

2,3,5-TRICHLOROPHENOL

933-78-8

 

skin

Inhalation: cough, sore throat

Skin: redness, pain

Eyes: redness, pain

Ingestion: convulsion, abdominal pain, diarrhoea, dizziness, headache, vomiting, weakness, fatigue, muscular spasms, increased body temperature and sweating

 

 

2,3,6-TRICHLOROPHENOL

933-75-5

eyes; skin; resp. tract

skin

Inhalation: cough, sore throat

Skin: redness, pain

Eyes: redness, pain

Ingestion: abdominal pain, diarrhoea, dizziness, headache, vomiting, weakness, fatigue, muscular spasms, increased body temperature and sweating

 

 

2,4,5-TRICHLOROPHENOL

95-95-4

eyes; skin; resp. tract

skin; liver; kidneys

Inhalation: cough, sore throat

Skin: may be absorbed, redness

Eyes: redness, blurred vision

Ingestion: abdominal pain, diarrhoea, dizziness, headache, vomiting, weakness, fatigue, sweating

 

 

2,4,6-TRICHLOROPHENOL

88-06-2

eyes; skin; resp. tract

liver

Inhalation: cough

Skin: may be absorbed, redness

Eyes: redness

Ingestion: diarrhoea, nausea, vomiting, weakness

 

 

 

___________________________________________________________________________

 

Table 104.139       Phenols & Phenolic Compounds: Physical & chemical hazards

 

For UN Class: 1.5 = very insensitive substances which have a mass explosion hazard; 2.1 = flammable gas; 2.3 = toxic gas; 3 = flammable liquid; 4.1 = flammable solid; 4.2 = substance liable to spontaneous combustion; 4.3 = substance which in contact with water emits flammable gases; 5.1 = oxidizing substance; 6.1 = toxic; 7 = radioactive; 8 = corrosive substance

 

CHEMICAL NAME

CAS-NUMBER

PHYSICAL

CHEMICAL

UN CLASS OR DIVISION /  SUBSIDIARY RISKS

CATECHOL

120-80-9

 

On combustion, forms acrid and irritating fumes  Reacts with oxidants

 

p-CHLORO-m-CRESOL

59-50-7

 

 

6.1

2-CHLOROPHENOL

95-57-8

The vapour is heavier than air

The substance decomposes on heating producing toxic and corrosive fumes (hydrochloric acid, chlorine)  Reacts with oxidants

6.1

3-CHLOROPHENOL

108-43-0

 

The substance decomposes on heating producing toxic and corrosive fumes (hydrochloric acid, chlorine)  Reacts with oxidants

 

4-CHLOROPHENOL

106-48-9

The vapour is heavier than air

The substance decomposes on heating producing toxic and corrosive fumes (hydrochloric acid, chlorine)  Reacts with oxidants

6.1

CRESOL, ALL ISOMERS

1319-77-3

 

The substance decomposes on heating producing strong acids and bases, causing fire and explosion hazard  Attacks many metals

6.1/ 8

o-CRESOL

95-48-7

 

On combustion, forms toxic fumes  Reacts violently with strong oxidizing agents, causing fire and explosion hazard  Easily oxidized on exposure to air

6.1/ 8

m-CRESOL

108-39-4

 

The substance decomposes on burning producing toxic and irritating fumes  Reacts with strong oxidants

6.1/ 8

p-CRESOL

106-44-5

 

On combustion, forms toxic fumes  Reacts violently with strong oxidizing agents, causing fire and explosion hazard

6.1/ 8

2,6-DI-tert-BUTYL-p-CRESOL

128-37-0

 

The substance decomposes on heating and on contact with oxidizing materials

 

2,4-DICHLOROPHENOL

120-83-2

The vapour is heavier than air

On combustion, forms corrosive gas (hydrogen chloride)  Reacts violently with strong oxidants  Gives off toxic fumes in a fire

6.1

2,5-DICHLOROPHENOL

583-78-8

 

The substance decomposes on burning producing irritating and poisonous gases  Reacts with oxidants, acid chlorides, acid anhydrides

6.1

3,5-DICHLOROPHENOL

591-35-5

 

The substance decomposes on burning producing irritating and poisonous gases, acid chlorides, acid anhydrides  Reacts with oxidants

6.1

2,4-DIMETHYLPHENOL

105-67-9

 

 

6.1

DINITRO-o-CRESOL

534-52-1

 

 

6.1

HYDROQUINONE

123-31-9

Dust explosion possible if in powder or granular form, mixed with air

Reacts violently with sodium hydroxide

6.1

2-HYDROXYBIPHENYL

90-43-7

Dust explosion possible if in powder or granular form, mixed with air

Producing carbon monoxide, acrid smoke and irritant fumes  Reacts with strong bases and strong oxidants

 

PENTACHLOROPHENOL

87-86-5

 

The substance decomposes on heating above 200 °C, producing toxic fumes and toxic gases including hydrogen chloride, dioxines, chlorinated phenols  Reacts violently with strong oxidants and water, causing fire and explosion hazard

6.1

PENTACHLOROPHENOL, SODIUM SALT

131-52-2

 

On contact with hot surfaces or flames this substance decomposes forming hydrocarbon chloride, chlorinated phenols, carbon monoxide, and   Reacts with strong oxidants causing fire and explosion hazard

6.1

PHENOL

108-95-2

The vapour is heavier than air and may travel along the ground; distant ignition possible

May explode on heating above 78 °C  On combustion, forms toxic fumes (carbon monoxide)  Upon heating, toxic fumes are formed  The solution in water is a weak acid  Reacts with oxidants causing fire and explosion hazard

6.1

PYROGALLIC ACID

87-66-1

 

Upon heating, toxic fumes are formed  The substance is a weak acid  Reacts with oxidants and bases

 

RESORCINOL

108-46-3

 

 

6.1

2,3,4,6-TETRACHLOROPHENOL

58-90-2

 

 

6.1

2,3,5,6-TETRACHLOROPHENOL

935-95-5

The vapour is heavier than air

The substance decomposes on heating and on contact with strong oxidants producing toxic and irritant vapours and fumes such as hydrogen chloride, phosgene  The substance is a weak acid

6.1

2,3,4-TRICHLORO PHENOL

15950-66-0

 

The substance decomposes on heating producing carbon monoxide, hydrogen chloride  Reacts with oxidants, acid anhydrides, and acid chlorides

 

2,3,5-TRICHLORO PHENOL

933-78-8

 

The substance decomposes on heating, on burning and on contact with strong oxidants producing toxic and irritant vapour and fumes (hydrogen chloride and phosgene)  The substance is a weak acid  Reacts with strong oxidants

 

2,3,6-TRICHLOROPHENOL

933-75-5

 

May explode on heating  The substance decomposes on heating, on contact with strong oxidants producing toxic and irritant vapours and fumes (hydrogen chloride and phosgene)  The substance is a weak acid  Reacts with strong oxidants

 

2,4,5-TRICHLOROPHENOL

95-95-4

 

May explode on heating to decomposition  The substance decomposes on heating and on contact with strong oxidants producing toxic and irritating fumes (chlorine, hydrochloric acid)  The substance is a weak acid  Reacts with strong oxidants  Reacts in an alkaline medium at high temperatures producing highly toxic chlorinated dioxins

 

2,4,6-TRICHLOROPHENOL

88-06-2

 

On combustion, forms toxic fumes (HCI, CO)  The substance decomposes on heating or on burning producing toxic and corrosive fumes (hydrogen chloride and chlorine)  Reacts violently with strong oxidants

 

 

___________________________________________________________________________

 

Table 104.140      Phenols & Phenolic Compounds: Physical & chemical properties

 

CHEMICAL NAME

CAS-NUMBER

COLOUR/FORM

BOILING POINT

(°C)

MELTING POINT

(°C)

MOLECULAR WEIGHT

SOLUBILITY IN WATER

RELATIVE DENSITY (WATER=1)

RELATIVE VAPOUR DENSITY (AIR=1)

VAPOUR PRESSURE/ (KPA)

INFLAM.

LIMITS

FLASH POINT (°C)

AUTO IGNITION POINT

(°C)

p-tert-BUTYLPHENOL

98-54-4

 

237

98

150.21

sol

0.908

@ 80 °C

 

 

 

 

 

4-tert-BUTYLPYROCATECHOL

98-29-3

 

285

53.5

166.21

 

 

 

 

 

 

 

CATECHOL

120-80-9

monoclinic tablets, prisms from toluene; colourless crystals; colourless crystals, discolours to brown on exposure to air and light, especially when moist

245

105

110.11

v sol

1.344

3.79

3x mm Hg

 

127 cc

510

p-CHLORO-m-CRESOL

59-50-7

dimorphous crystals; needles from petroleum ether; white or slightly pink crystals

235

67

142.58

sl sol

 

 

 

 

 

 

2-CHLOROPHENOL

95-57-8

light amber liquid; colourless to yellow brown liquid

174.9

9.3

128.6

sl sol

1.2634

4.4

0.23

 

64 cc

 

3-CHLOROPHENOL

108-43-0

needles; white crystals

214

33

128.6

sl sol

1.268

@25°C

 

0.13

@ 44.2°C

 

>112

 

4-CHLOROPHENOL

106-48-9

needle like, white to straw-coloured crystals; pink crystals

220

43

128.6

sl sol

1.2238

@ 78°C/4°C

4.43

13 Pa

 

121 cc

 

CRESOL, ALL ISOMERS

1319-77-3

colourless, yellowish, brownish-yellow, or pinkish liquid

191-203

11-35

108.13

50 parts

1.030-1.038

@ 25°C/ 25 °C

3.72

14-32 Pa

@ 25 °C

1.1 ll

? ul

43-82

559

o-CRESOL-

95-48-7

colourless crystalline compound; white crystals/liquid

191

31

108.1

sol

1.047

3.72

33 Pa

@ 25 °C

1.35 ll

? ul

81 cc

599

m-CRESOL

108-39-4

colourless or yellowish liquid

202

12

108.1

sl sol

1.034

3.72

20 Pa

@ 25 °C

1.1 ll

? ul

86 cc

558

p-CRESOL

106-44-5

crystals; prisms; colourless; white crystals; crystalline mass

201.9

35

108.13

sl sol

1.0178

3.72

15 Pa

@ 25 °C

1.1 ll

? ul

86 cc

559

2,6-DI-tert-BUTYL-p-CRESOL

128-37-0

white crystalline solid; pale yellowish crystalline powder

265

70

220.34

insol

1.048

7.6

 

 

127 cc

 

2,6-DI-tert-BUTYLPHENOL

128-39-2

 

133

39

206.31

 

 

 

 

 

 

 

2,4-DICHLOROPHENOL

120-83-2

colourless crystals; hexagonal needles from benzene; white solid

210

45

163.00

sl sol

1.383

@ 60°C/25°C

5.62

0.075 mm Hg

@ 25.0°C

 

114

 

2,5-DICHLOROPHENOL

583-78-8

prisms from benzene & petroleum ether

211

@ 744 mm Hg

59

163.0

sl sol

 

5.6

16.6 Pa

@ 25°C

 

 

 

3,5-DICHLOROPHENOL

591-35-5

prisms from petroleum ether

233

@ 757 mm Hg

68

163.00

sl sol

 

5.6

1.1 Pa

@ 25°C

 

 

 

2,4-DIMETHYLPHENOL

105-67-9

crystals; needles from water; colourless needles

211.5

@ 766 mm Hg

25.4-26

122.16

sl sol

0.9650

 

10 mm Hg

@ 92.3 °C

 

 

 

DINITRO-o-CRESOL

534-52-1

 

312

87

198.13

sl sol

 

6.8

1.05x mm Hg

@ 25 °C

 

 

 

HYDROQUINONE

123-31-9

colourless, hexagonal prisms; white crystals; monoclinic prisms (sublimation); needles from water; prisms from methanol

285-287

172

110.11

sol

1.332

3.81

0.12 Pa

 

165

515

2-HYDROXYBIPHENYL

90-43-7

needles from petroleum ether; pinkish crystals; white, flaky crystals; colourless crystals

286

59

170.20

insol

1.213

@ 25 °C/4 °C

 

2.7

@ 163 °C

 

124 cc

530

4-METHOXYPHENOL

150-76-5

plates from water; white waxy solid

243

57

124.14

sol

1.55

 

 

 

132 oc

421

NONYLPHENOL, ALL ISOMERS

25154-52-3

thick light yellow, straw coloured liquid

293-297

-10

220.39

insol

0.950

7.59

<0.01

1.0 ll

? ul

140 cc

370

PENTACHLOROPHENOL

87-86-5

colourless crystals (pure); dark greyish powder or flakes (crude product); solid beads or flakes; white monoclinic, crystalline solid; needle-like crystals

309-310

190-191

266.3

sl sol

1.978

@ 22°C/4°C

9.20

0.02 Pa

 

 

 

PENTACHLOROPHENOL, SODIUM SALT

131-52-2

buff coloured flakes; white or tan powder

 

 

288.34

33%

@ 25°C

 

 

 

 

 

 

PHENOL

108-95-2

colourless, acicular crystals or white, crystalline mass; colourless to light pink, interlaced, or separate, needleshaped crystals, or a light pink, crystalline mass

181.8

43

94.11

sol

1.0576

3.24

47 Pa

1.7 ll

8.6 ul

79 cc

715

PYROGALLIC ACID

87-66-1

white crystals; orthorhombic; leaflets or needles from benzene

309

133

126.11

v sol

1.45

 

1.33

@ 168 °C

 

 

 

RESORCINOL

108-46-3

white needle-like crystals; needles from benzene; plates from water; rhombic tablets & pyramids; powder

280

111

110.11

sol

1.2717

1.0739

1 mm Hg

@ 108.4 °C

1.4

@ 200 °C ll

? ul

 

 

2,3,4,6-TETRACHLOROPHENOL

58-90-2

needles from ligroin, acetic acid; brown flakes or sublimed mass; light brown mass

150

@ 15 mm Hg

70

231.89

insol

1.83

@ 25°C/4°C

 

1 mm Hg

@ 100.0°C

 

 

 

2,3,5,6-TETRACHLOROPHENOL

935-95-5

leaf, from ligroin

288

115

231.89

sl sol

1.7

8.1

<10 Pa

 

 

 

4,4’-THIO-BIS-(6-tert-BUTYL-M-CRESOL)

96-69-5

light grey powder; fine white crystals

 

150

358.58

0.08%

 

 

 

 

 

 

2,3,4-TRICHLOROPHENOL

15950-66-0

white powder or needles

 

83.5 sublimes

197.5

 

 

 

 

 

 

 

2,3,5-TRICHLOROPHENOL

933-78-8

colourless crystals

248-249

62

197.4

insol

 

6.8

 

 

 

 

2,3,6-TRICHLOROPHENOL

933-75-5

needles from diluted alcohol, petroleum ether; colourless needles

253

58

197.44

sl sol

1.5

6.82

 

 

78

 

2,4,5-TRICHLOROPHENOL

95-95-4

needles from alcohol or ligroin; gray flakes in sublimed mass; colourless needles

253

67

197.4

sl sol

1.678

@ 25°C/4°C

 

2.9 Pa

@ 25°C

 

 

 

2,4,6-TRICHLOROPHENOL

88-06-2

crystals from ligroin; yellow flakes; rhombic needles from acetic acid; colourless needles

246

69

197.45

800 mg/l

@ 25°C

1.4901

6.8

133 Pa

@ 76.5°C

 

 

 

 

___________________________________________________________________________