4-Cumylphenol

212.29

212.29

209-968-0

2RLA3OL3QT

6237

DTXSID3022536

White to tan crystals|Prisms from petroleum ether

29071990

20.2

3.7

DryPowder; Liquid; OtherSolid

1.0163 g/cm³ @ Temp: 20 °C

73 °C

213-214 °C @ Press: 25 Torr

160ºC

1.587

2.5X10-5 mm Hg at 25 deg C (extrapolated)

Characteristic phenol odor

Henry's Law constant = 8.8X10-8 atm-cu m/mol at 25 °C (est)

pka = 10.0 at 25 °C (est)

Hydroxyl radical reaction rate constant = 4.5X10-11 cu cm/molecule-sec at 25 °C (est)

Critical temperature: 834 K; critical pressure: 2.86X10+6 Pa (est)

2

R36/37/38

24/25-37/39-26

SL1942450

Xi

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

P201, P202, P260, P264, P270, P273, P281, P301+P312, P308+P313, P314, P330, P391, P405, P501

H302

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

|Warning|H302 (10.61%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 133 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P264, P270, P281, P301+P312, P308+P313, P314, P330, P405, and P501

A phenol, 4-(1-methyl-1-phenethyl)- concentration of <0.01 to 0.49 ug/L was detected in the manifold exhaust gases from a polycarbonate processing extruder inside a polycarbonate processing facility(1).

LD50 Rat oral 1770 mg/kg bw|LD50 Frog oral 335 mg/kg

Phenol, 4-(1-methyl-1-phenethyl)-'s production and use as an intermediate for resins, insecticides and lubricants(1) and its major use as a chain terminator for polycarbonates(2) may result in its release to the environment through various waste streams(SRC). Another application involves its reaction with ethylene oxide to form a specialty surfactant(2); it has been reported to be a detergent metabolite(3).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.9X10+4(SRC), determined from a structure estimation method(2), indicates that phenol, 4-(1-methyl-1-phenethyl)- is expected to be immobile in soil(SRC). The estimated pKa of phenol, 4-(1-methyl-1-phenethyl)- is 10.0(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of phenol, 4-(1-methyl-1-phenethyl)- from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.8X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Phenol, 4-(1-methyl-1-phenethyl)- is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 2.5X10-5 mm Hg at 25 °C(5). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(6) suggests that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.9X10+5(SRC), determined from a structure estimation method(2), indicates that phenol, 4-(1-methyl-1-phenethyl)- is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 8.8X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 240(SRC), from an estimated log Kow of 4.12(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). However, phenol, 4-(1-methyl-1-phenethyl)- is reported to have low bioconcentration based on test results using catfish(5). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(6)suggests that biodegradation is not an important environmental fate process in water(SRC). Phenol, 4-(1-methyl-1-phenethyl)- is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Phenols can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl and peroxy radicals with half-lives on the order of days to weeks at the water surface(7); therefore, photo-oxidation may have some importance as a fate process for phenol, 4-(1-methyl-1-phenethyl)- in natural water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phenol, 4-(1-methyl-1-phenethyl)-, which has an extrapolated vapor pressure of 2.5X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase phenol, 4-(1-methyl-1-phenethyl)- 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 9 hours(SRC), calculated from its rate constant of 4.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase phenol, 4-(1-methyl-1-phenethyl)- may be removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of phenol, 4-(1-methyl-1-phenethyl)- with photochemically-produced hydroxyl radicals has been estimated as 4.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Phenol, 4-(1-methyl-1-phenethyl)- is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Phenols can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl and peroxy (RO2) radicals with half-lives on the order of days to weeks at the water surface(3); therefore, photo-oxidation may have some importance as a fate process for phenol, 4-(1-methyl-1-phenethyl)- in natural water(SRC).

An estimated BCF of 240 was calculated in fish for phenol, 4-(1-methyl-1-phenethyl)-(SRC), using an estimated log Kow of 4.12(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC). However, phenol, 4-(1-methyl-1-phenethyl)- is reported to have low bioconcentration based on test results using catfish(3).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of phenol, 4-(1-methyl-1-phenethyl)- can be estimated to be 2.9X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that phenol, 4-(1-methyl-1-phenethyl)- is expected to be immobile in soil. The estimated pKa of phenol, 4-(1-methyl-1-phenethyl)- is 10.0(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

The Henry's Law constant for phenol, 4-(1-methyl-1-phenethyl)- is estimated as 8.8X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that phenol, 4-(1-methyl-1-phenethyl)- is expected to be essentially non-volatile from water surfaces(2). Phenol, 4-(1-methyl-1-phenethyl)-'s Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Phenol, 4-(1-methyl-1-phenethyl)- is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 2.5X10-5 mm Hg at 25 °C(3).

SURFACE WATER: Phenol, 4-(1-methyl-1-phenethyl)- was not detected (reporting limit of 1 ug/L) in 76 samples water samples collected upstream and downstream from selected towns and cities in Iowa in 2001(1). Phenol, 4-(1-methyl-1-phenethyl)- concentrations of 0.016 to 0.053 were quantified in three water samples collected from the Rhine River delta, The Netherlands in 1989(2).

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of phenol, 4-(1-methyl-1-phenethyl)- is 1000 or greater; the data may be greatly underestimated(1).|Occupational exposure to phenol, 4-(1-methyl-1-phenethyl)- may occur through inhalation and dermal contact with this compound at workplaces where phenol, 4-(1-methyl-1-phenethyl)- is produced or used. Since phenol, 4-(1-methyl-1-phenethyl)- has been identified as a detergent metabolite(1), the general population may be exposed via dermal contact with wastewaters or surface waters containing phenol, 4-(1-methyl-1-phenethyl)-(SRC).

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/ENDOCRINE MODULATION/ A receptor-binding assay and X-ray crystal structure analysis demonstrated that the endocrine disruptor bisphenol A (BPA) strongly binds to human estrogen-related receptor gamma (ERRgamma). BPA is well anchored to the ligand-binding pocket, forming hydrogen bonds with its two phenol-hydroxyl groups. In this study, /the researchers/ found that 4-alpha-cumylphenol lacking one of its phenol-hydroxyl groups also binds to ERRgamma very strongly. The 2.0 A crystal structure of the 4-alpha-cumylphenol/ERRgamma complex clearly revealed that ERRgamma's Leu345-beta-isopropyl plays a role in the tight binding of 4-alpha-cumylphenol and BPA, rotating in a back-and-forth induced-fit manner. PMID:18582436

4-cumylphenol

Petroleum refineries|Phenol, 4-(1-methyl-1-phenylethyl)-: ACTIVE

Method: USGS-NWQL O-1433-01; Procedure: gas cromatography/mass spectrometry; Analyte: 4-cumylphenol; Matrix: filtered wastewater and natural-water samples; Detection Limit: 0.37 ug/L.