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Home > Encyclopedia > 2-Ethylphenol

2-Ethylphenol

2-Ethylphenol structure

2-Ethylphenol 

structure
  • CAS No:

    90-00-6

  • Formula:

    C8H10O

  • Chemical Name:

    2-Ethylphenol

  • Synonyms:

    Phenol,2-ethyl-;Phenol,o-ethyl-;2-Ethylphenol;o-Ethylphenol;Phlorol;1-Ethyl-2-hydroxybenzene;NSC 10112;o-Hydroxyethylbenzene

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

colourless liquid


Ethylphenol is a yellow liquid. Freezing point -18°C. Flash point 172°F.|Liquid


Ethylphenol is a yellow liquid. Freezing point -18°C. Flash point 172°F.|2-Ethylphenol is a member of phenols.

2-Ethylphenol Basic Attributes

122.164

122.16

607-726-2

355O0P4JU7

10112

3145

DTXSID1022479

METASTABLE & STABLE CRYSTAL FORM|COLORLESS LIQUID

2907199090

Characteristics

20.23000

2.47

Ethylphenol is a yellow liquid. Freezing point -18°C. Flash point 172°F.

1.0146 g/cm3 @ Temp: 25 °C

18 °C

204.5 °C

78.3±0.0 °C

1.537

insoluble

0.153 mm Hg at 25 deg C.

Phenol odor

pK = 10.2

Cooling the liquid to -30 °C gives a metastable cryst form, mp about -28 °C; when kept for 24-48 hrs, this changes to the stable cryst form, mp -3.4 °C.

Insoluble in water.

Phenols and Cresols

ETHYLPHENOL is incompatible with acid chlorides, acid anhydrides and oxidizing agents. (NTP, 1992). Weakly acidic.

Safety Information

III

8

UN 3145 8/PG 2

3

R20/21/22;R34

S36/37/39-S45-S26

SL4025000

C:Corrosive

Stable. Combustible. Incompatible with acid chlorides, acid anhydrides, oxidizing agents.

P261-P280-P305 + P351 + P338

H302-H315-H318-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.

Special Hazards of Combustion Products: Emits toxic fumes under fire conditions. (USCG, 1999)

|Danger|H302 (64.94%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 462 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Not Classified|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P305+P351+P338, P310, P330, and P501|Warning|H227: Combustible liquid [Warning Flammable liquids]|P210, P264, P270, P280, P301+P312, P330, P370+P378, P403+P235, and P501

Fire Extinguishing Agents: Carbon dioxide, dry chemical, alcohol foam. (USCG, 1999)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Neutralizing Agents for Acids and Caustics: Dry lime or soda ash. (USCG, 1999)

Wear self-contained breathing apparatus, rubber boots and heavy rubber gloves. (USCG, 1999)

2-Ethylphenol was detected in industrial wastewater from the following industries: petroleum refining (1 of 21 extracts), electronics (1 of 32 extracts), and publicly-owned treatment works (1 in 44 extracts)(1). 2-Ethylphenol was detected in a sample of finished drinking water from a plant in Philadelphia, PA, in February 1976(2). Wastewater from the gasification of Indian Head lignite coal in North Dakota contained 2-ethylphenol at an estimated concentration of 50 mg/L(3). 2-Ethylphenol was measured in coal conversion wastewaters for two different synthanes at 140-170 and 2185 mg/L(4).

Toxicity

EXTRACTED FROM THE WOOD OF OAK TREES. ORTHO- & PARA-ETHYLPHENOL WERE IDENTIFIED.

2-Ethylphenol's production and use as a starting material for photochemicals(1) may result in its release to the environment through various waste streams(SRC). 2-Ethylphenol is also released in effluent streams from coal gasification plants(2,3).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 530(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that 2-ethylphenol will have low to moderate mobility in soil(SRC). Limited data suggests that biodegradation of this compound under both aerobic(4) and anaerobic conditions(5) may be possible. 2-Ethylphenol's values for vapor pressure(6) and Henry's Law constant(6,7,SRC) indicate that volatilization from dry and moist soil surfaces is possible, but is not likely to be a major fate process for this compound(SRC).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 530(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that 2-ethylphenol may adsorb to suspended solids and sediment(SRC) in the water column. Limited data suggest that biodegradation of this compound under both aerobic(4) and anaerobic conditions(5) may be possible. 2-Ethylphenol should volatilize from water surfaces based on an estimated Henry's Law constant of 4.6X10-6 atm-cu m/mole(SRC), from its experimental values for vapor pressure(6), and water solubility(7). Estimated half-lives for a model river and model lake are 9 and 68 days, respectively(3,SRC). An estimated BCF value of 44(3,SRC), from a measured log Kow(2), suggests that bioconcentration of 2-ethylphenol in aquatic organisms is moderate(SRC) according to a recommended classification scheme(8).|ATMOSPHERIC FATE: According to a suggested classification scheme(1), a measured vapor pressure of 0.153 mm Hg at 25 °C(2) indicates that 2-ethylphenol will mainly exist in the vapor phase in the ambient atmosphere. Vapor-phase 2-ethylphenol is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 9 hours(3,SRC).

The rate constant for the vapor-phase reaction of 2-ethylphenol with photochemically produced hydroxyl radicals has been estimated as 4.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). 2-Ethylphenol has a measured pKa of 10.2, indicating that under most environmental conditions this compound will exist mainly as the non-dissociated form(2).

An estimated BCF value of 44 was calculated for 2-ethylphenol(SRC), using a measured log Kow of 2.47(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is moderate, not high(SRC).

The Koc of 2-ethylphenol is estimated as approximately 530(SRC), using a measured log Kow of 2.47(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 2-ethylphenol has moderate to low mobility in soil(SRC).

The Henry's Law constant for 2-ethylphenol is estimated as 4.6X10-6 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 0.153 mm Hg at 25 °C(1), and water solubility, 5340 mg/L at 25 °C(2). This value indicates that 2-ethylphenol will volatilize from water surfaces(3,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 9 days(3,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 68 days(3,SRC). 2-Ethylphenol's values for vapor pressure(1) and estimated Henry's Law constant(1,2,SRC) indicate that volatilization from dry and moist soil surfaces is possible, but is not likely to be a major fate process for this compound(SRC).

GROUNDWATER: 2-Ethylphenol was present in groundwater taken from a coal tar distillation and wood-treatment plant at St. Louis Park, MN at 0.44 mg/l(1). Groundwater collected at different depths at an abandoned creosote works, Pensacola, FL contained 2-ethylphenol at concentrations of 0.07-0.33 mg/l (depths of 3.3-11 m)(1). 2 of 10 wells sampled at Gas Works Park (a former site of a coal gasification and oil gasification plant) contained 2-ethylphenol at concentrations of 0.1 and 0.15 mg/l (detection limit = 0.005 mg/l)(2).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 93 workers (56 of these are female) are potentially exposed to 2-ethylphenol in the USA(1). Thermal decomposition products which were released during the use of powder paint (an amine-cured epoxy powder paint is applied to metal objects and a protective film is formed by exposing the object to high temperatures) included 2-ethylphenol(2). The general population may be exposed via dermal contact or the inhalation of air containing this compound(SRC).

Drug Information

ANALYSES OF BLOOD & URINE OF 4 FEMALES OCCUPATIONALLY EXPOSED TO MIXT OF XYLENES & ETHYLBENZENE IN A HISTOLOGY LAB. APPROX 1.1-1.4% OF RETAINED ETHYLBENZENE WAS METABOLIZED TO 2-ETHYLPHENOL.|3 LAB TECHNICIANS EXPOSED TO ETHYLBENZENE 42 PPM & 1 EXPOSED TO 34 PPM HAD AVG STEADY STATE BLOOD LEVELS OF 0.72 + OR - 0.11 MG/L. AMT DECR. METABOLITES IDENTIFIED INCL 2-ETHYLPHENOL.

Harmful if swallowed, inhaled, or absorbed through skin. Irritating to mucous membranes, upper respiratory tract, eyes and skin. Can cause damage to the eyes and severe irritation or burn. (USCG, 1999)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Phenols are very toxic poisons AND corrosive and irritating, so that inducing vomiting may make medical problems worse. IMMEDIATELY call a hospital or poison control center and locate activated charcoal, egg whites, or milk in case the medical advisor recommends administering one of them. If advice from a physician is not readily available and the victim is conscious and not convulsing, give the victim a glass of activated charcoal slurry in water or, if this is not available, a glass of milk, or beaten egg whites and IMMEDIATELY transport victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, assure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

/TOXICITY/...SIMILAR TO, BUT LESS SEVERE THAN, PHENOL.

2-ethylphenol

2-Ethylphenol Use and Manufacturing

Methods of Manufacturing

PREPN: ...HEATING ETHYLENE & PHENOL WITH PHOSPHORIC ACID @ 200 °C; BY HEATING ETHANOL & PHENOL OVER THORIA + ALUMINA @ 350 °C; FROM PHENOL, ETHYLENE CHLOROHYDRIN & SODIUM.|2-Ethylphenol is produced industrially by ortho-alkylation of phenol with ethylene in high pressure autoclaves at 320-340 °C and 20 Mpa in the presence of 1-2% aluminum phenolate. If a molar ratio of phenol-ethylene of ca. 1:2 is used, the yield (related to converted phenol) is ca. 32% 2-ethylphenol ... after 6 hour reaction time.

Uses

Solvents (for cleaning and degreasing)


Automotive care products

Production

1,000,000 - 10,000,000 lb

All other chemical product and preparation manufacturing|Phenol, 2-ethyl-: ACTIVE|2-METHYLPHENOLS & A NUMBER OF RELATED DERIV WERE PREPARED & TESTED FOR BACTERIOSTATIC ACTIVITY AGAINST A VARIETY OF BACTERIA, & STRUCTURAL-BIOLOGICAL ACTIVITY RELATIONS WERE INDICATED.

SIMPLE & RAPID GAS LIQ SOLID CHROMATOGRAPHIC METHOD IS PRESENTED FOR DETERMINATION OF TRACE AMT (AT PPB LEVELS) OF 11 PHENOLS IN AIR USING TENAX-GC PRECOLUMN & TENAX-GC PLUS ALKALINE PRECOLUMN. METHOD WAS APPLIED TO SPECIMENS OF AMBIENT AIR NEAR A FACTORY & URBAN AIR IN JAPAN.|SEPARATION OF 13 ISOMERIC ALKYLPHENOLS WAS STUDIED BY HIGH PERFORMANCE LIQ, GLC & HIGH PERFORMANCE THIN-LAYER CHROMATOGRAPHIC TECHNIQUES.|2-Ethylphenol was measured in environmental waters using reverse-phase liquid chromatography with electrochemical detection.|2-Ethylphenol was measured in hazardous waste samples using GC/MS followed by two Fourier-transform infrared techniques and analysis by the Program for Automated Waste Mixture Interpretation.

Food additives -> Flavoring Agents

Flavoring Agents

Computed Properties

Molecular Weight:122.16
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:122.073164938
Monoisotopic Mass:122.073164938
Topological Polar Surface Area:20.2
Heavy Atom Count:9
Complexity:80.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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