4-tert-Butylphenol
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4-tert-Butylphenol
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CAS No:
98-54-4
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Formula:
C10H14O
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Chemical Name:
4-tert-Butylphenol
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Synonyms:
Phenol,4-(1,1-dimethylethyl)-;Phenol,p-tert-butyl-;4-(1,1-Dimethylethyl)phenol;Butylphen;p-tert-Butylphenol;4-tert-Butylphenol;PTBP;NSC 3697;B 110666;1334243-56-9
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CAS No:
Description
4-tert-Butylphenol is a white to pale yellow crystalline solid at room temperature and is sold in solid form as flakes or briquettes. 4-tert-butylphenol is employed in coating products, polymers, adhesives, sealants and for the synthesis of other substances.
The major use is as a monomer in chemical synthesis, e.g. for the production of polycarbonate, phenolic resins, epoxy resins. PtBP is used as a chain terminator in the synthesis of polycarbonate polymers. The main uses of polycarbonat
Crystals or practically white flakes. Has a disinfectant-like odor. May float or sink in water. Insoluble in water. (NTP, 1992)|DryPowder; Liquid; OtherSolid; PelletsLargeCrystals; PelletsLargeCrystals, Liquid|Solid|WHITE HYGROSCOPIC FLAKES.|White needle-like crystals, phenolic odour|Crystals or white flakes with disinfectant-type odor.
Crystals or practically white flakes. Has a disinfectant-like odor. May float or sink in water. Insoluble in water. (NTP, 1992)|4-tert-butylphenol is a member of the class of phenols that is phenol substituted with a tert-butyl group at position 4. It has a role as an allergen.
4-tert-Butylphenol Basic Attributes
150.221
150.22
202-679-0
O81VMW36CV
0637
3697
2430
DTXSID1020221
Needles from water|Needles from lignin|White crystals|Crystals, needles, or practically white flakes
2907199090
Characteristics
20.2
2.4/3.4
Crystals or practically white flakes. Has a disinfectant-like odor. May float or sink in water. Insoluble in water. (NTP, 1992)
0.9 g/cm3
98 °C
237 °C
115°C o.c.
1.514
H2O: 8.7 g/L (20 ºC)
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from moisture.
Vapour pressure, Pa at 50°C: 30
5.1 (NTP, 1992) (Relative to Air)
LD50 orally in rats: 3.25 ml/kg (Smyth)
Distinctive odor
1.19e-06 atm-m3/mole|Henry's Law constant = 1.19X10-6 atm-cu m/mole at 25 °C
pKa = 10.16 at 25 °C (OECD Guideline 112)
Volatile with steam|Vapor Pressure: 0.00375 mm Hg at 20 °C|Hydroxyl radical reaction rate constant = 4.1X10-11 cu-cm/molc sec at 25 °C (est)
Insoluble in water.
Phenols and Cresols
Phenols, such as 4-TERT-BUTYL PHENOL, do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has pKa = 9.88). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid.
-16,900 Btu/lb = -9,410 cal/g = -394 X 105 J/kg
67.9 kJ/mol
Safety Information
III
8
UN 3077 9/PG 3
2
R37/38;R41;R51/53
S26-S39-S61
SJ8925000
Xi:Irritant;N:Dangerousfortheenvironment;
Well closed.
Stable. Incompatible with copper, steel, bases, acid chlorides, acid anhydrides, oxidizing agents.
P201-P273-P280-P305 + P351 + P338 + P310-P308 + P313-P501
H315-H318-H361f-H411
SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.
Incompatible materials: Bases, acid chlorides, acid anhydrides, oxidizing agents, brass, copper.
Combustible. (NTP, 1992)|Combustible.
|Danger|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P264, P273, P280, P281, P302+P352, P305+P351+P338, P308+P313, P310, P321, P332+P313, P362, P391, P405, and P501|H314 (12.46%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P201, P202, P260, P261, P264, P271, P272, P273, P280, P281, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 3756 companies from 69 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P261, P264, P271, P273, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P332+P313, P362, P391, P403+P233, P405, and P501|P260, P261, P264, P270, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P310, P312, P314, P321, P332+P313, P333+P313, P362, P363, P403+P233, P405, and P501
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)
SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. RECOMMENDED GLOVE MATERIALS: Permeation data indicate that butyl rubber gloves may provide protection to contact with this compound. Butyl rubber over latex gloves is recommended. However, if this chemical makes direct contact with your gloves, or if a tear, hole or puncture develops, remove them at once. (NTP, 1992)|Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166 (EU).|Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Combustible when exposed to heat or flame.
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Provide appropriate exhaust ventilation at places where dust is formed.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|For more Preventive Measures (Complete) data for p-tert-Butylphenol (6 total), please visit the HSDB record page.
Irritant to eyes and skin.|A skin and severe eye irritant
Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Well closed.
Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
The substance is severely irritating to the eyes, skin and respiratory tract. The substance may cause effects on the skin. This may result in depigmentation.
Repeated or prolonged contact with skin may cause dermatitis. Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the liver, spleen, thyroid and nervous system. This may result in impaired functions.
NO open flames.
PREVENT DISPERSION OF DUST! STRICT HYGIENE!
Use local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear safety goggles or eye protection in combination with breathing protection.
Leachate samples collected at four landfills in the Gothenburg region, Sweden had a median p-tert-butylphenol concentration of 0.97 ug/L (range of 0.027-8.1 ug/L)(1). Leachate samples collected from a municipal landfill in Gryta, Sweden in May 1990 contained tert-butylphenol(2). p-tert-Butylphenol was qualitatively detected in trench leachate samples collected from low-level radioactive waster disposal sites at Maxey Flats, KY and West Valley, NY(3). p-tert-Butylphenol was detected in the influent to a waste treatment facility in North Carolina (possibly due to its use as a detergent constituent)(4). p-tert-Butylphenol was detected in emissions from incinerators(5). Untreated wastewater and septage samples from Cod Cod, MA (1996-1997 sampling) contained p-tert-butylphenol concentrations of 2.2-3.5 and 0.16-3.9 ug/L respectively(6).
SEDIMENT: Analysis of sediment samples taken from the Elbe River, Germany, and tributaries in 1998 identified p-tert-butylphenol concentrations of 19-82 ug/kg dry mass(1).
URBAN/SUBURBAN: p-tert-Butylphenol was detected in outdoor air from Tokyo, Japan(1).|INDOOR AIR: Indoor air samples collected from houses and offices in Tokyo, Japan contained maximum p-tert-butylphenol concentrations of 387 ng/cu m and a detection frequency of >97%(1); concentrations were higher in indoor air compared to outdoor air(1).
Polycarbonates have a residual free p-tert-butylphenol concentration of <5 ppm; however, cured epoxy systems may still contain significant amounts of unreacted p-tert-butylphenol (up to 5-10%)(1).
Toxicity
IDENTIFICATION AND USE: p-tert-Butylphenol (4-TBP) is a solid. It is used as a plasticizer for cellulose acetate, intermediate for antioxidants, special starches, oil-soluble phenolic resins, as a pour-point depressors and emulsion breakers for petroleum oils and some plastics, as a synthetic lubricants, industrial odorants, and motor-oil additives. It is no longer used as insecticide. HUMAN STUDIES: In a routine test series of the North American Contact Dermatitis Group in 1,900 patients with contact dermatitis revealed 1.9% positive reactions and the test series with 900-2,000 contact dermatitis patients revealed 1.1% positive reactions to 2% of 4-TBP. Ten shoemakers with eczema due to occupational exposure to 4-TBP containing glues were patch-tested for sensitization. Positive reactions to the glue, its ingredients and 4-TBP were observed in all patients. After 24 hours, reaction in the 4-TBP test was erythema, edema or papules, and some patients showed a few vesicles. After 48 hours, all patients showed these symptoms. In the search for environmental compounds responsible for contact or occupational vitiligo, it was found that the most potent was 4-TBP. In vitro 4-TBP induced oxidative stress that was more readily overcome by melanocytes from normally pigmented individuals than from two individuals with vitiligo. ANIMAL STUDIES: Sluggishness, unsteady gait, prostration, unkempt appearance, and nasal discharge were observed as the principal signs of toxicity in acute studies in rats. After inhalation exposure in rats, clinical signs observed on the day of exposure and up to 7 days after it included mucosal irritation and respiratory distress. Male hamsters given a 15 g/kg in a diet developed hyperplasia in the forestomach and papillomatous lesions. Male rats given a 15 g/kg in a diet for 51 weeks developed forestomach hyperplasia, but no tumors in the other organs. there were no treatment related toxic effects on pregnant and lactating females or their offspring in developmental studies in rats. 4-TBP did not induce gene mutation in S. Typhimurium TA100, TA98, TA1535, TA1537 and E. coli WP2 uvrA with and without exogenous metabolic activation system. However, 4-TBP induced both structural and numerical chromosome aberrations in vitro.
LD50 Rat oral 4,000 mg/kg|LD50 Rabbit dermal 2,318 mg/kg|LD50 Rat ip 225 mg/kg|LD50 Rat oral 3.25 mL/kg|For more Non-Human Toxicity Values (Complete) data for p-tert-Butylphenol (6 total), please visit the HSDB record page.
Vitiligo presents with depigmented cutaneous lesions following localized melanocyte death. Multiple factors contribute to cell death, including genetically determined susceptibility to trauma, and environmental factors, such as exposure to 4-tert-butylphenol (4-TBP). We demonstrate that 4-TBP induces oxidative stress that is more readily overcome by melanocytes from normally pigmented individuals than from two individuals with vitiligo. The antioxidant catalase selectively and significantly reduced death of melanocytes derived from two individuals with vitiligo, indicating a role for oxidative stress in vitiligo pathogenesis. In normal melanocytes, oxidative stress results in reduced expression of microphthalmia-associated transcription factor (MITF). Melanocyte-stimulating hormone-induced expression of MITF protein caused increased sensitivity to 4-TBP, whereas sensitivity of melanomas correlated with MITF expression. MITF stimulates melanin synthesis by up-regulating expression of melanogenic enzymes such as tyrosinase-related protein-1 (Tyrp1). Although melanin content per se did not affect sensitivity to 4-TBP, expression of Tyrp1 significantly increased sensitivity. Melanocytes and melanomas that express functional Tyrp1 were significantly more sensitive to 4-TBP than Tyrp1-null cells. Thus, normal melanocytes respond to 4-TBP by reducing expression of MITF and Tyrp1. We hypothesize that melanocytes in vitiligo demonstrate reduced ability to withstand oxidative stress due, partly, to a disruption in MITF regulation of Tyrp1.
p-tert-Butylphenol's production and use as a chemical intermediate for a variety of applications and as a plasticizer for cellulose acetate(1,2) may result in its release to the environment through various waste streams(SRC). The major use is in chemical synthesis for the production of polycarbonate, phenolic resins, epoxy resins(2). Small amounts of unreacted p-tert-butylphenol can exist in polycarbonate and resin products(2) and p-tert-butylphenol has been detected in landfill leachates(3). p-tert-Butylphenol has been detected in combustion emissions from incinerators(4).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1290(SRC), determined from a structure estimation method(2), indicates that p-tert-butylphenol is expected to have low mobility in soil(SRC). The pKa of p-tert-butylphenol is 10.16(3), indicating that this compound will exist almost entirely in the neutral form in the environment. Volatilization of p-tert-butylphenol from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 1.19X10-6 atm-cu m/mole(4). p-tert-Butylphenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.00919 mm Hg at 25 °C(5). Results of biodegradation screen tests suggest p-tert-butylphenol can be readily biodegradable via adapted microorganisms and at concentrations below inhibitory effects(6). Therefore, biodegradation is expected to be an important fate process(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1290(SRC), determined from a structure estimation method(2), indicates that p-tert-butylphenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.19X10-6 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 38 and 279 days, respectively(SRC). According to a classification scheme(5), a measured BCF range of 20-120(6,7), suggests the potential for bioconcentration in aquatic organisms is low to moderate(SRC). Results of biodegradation screen tests suggest p-tert-butylphenol can be readily biodegradable via adapted microorganisms and at concentrations below inhibitory effects(8). Therefore, biodegradation is expected to be an important fate process(SRC). p-tert-Butylphenol was found to be stable to hydrolysis at pH 4, pH 7 and pH 9 using OECD Guideline 111(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), p-tert-butylphenol, which has a vapor pressure of 0.00919 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase p-tert-butylphenol 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 9.5 hours(SRC), calculated from its rate constant of 4.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). p-tert-Butylphenol absorbs at wavelengths >290 nm(4,5) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of p-tert-butylphenol with photochemically-produced hydroxyl radicals has been estimated as 4.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 9.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the estimated OH radical reaction of p-tert-butylphenol with hydroxyl radicals in aqueous solutions at pH 9 is 1.9X10+10 L/mol-sec(2); this corresponds to an aquatic half-life of 42 days at an aquatic concentration of 1X10-17 hydroxyl radicals per liter(3). p-tert-Butylphenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). Using OECD Guideline 111, p-tert-butylphenol was found to be stable to hydrolysis at pH 4, pH 7 and pH 9(5). p-tert-Butylphenol absorbs in the UV region at wavelengths >290 nm(5,6) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). In a photodegradation test where p-tert-butylphenol was adsorbed to silica gel and irradiated with light >290nm, 46.8% was degraded(7). Direct photolysis of p-tert-butylphenol was found to yield 4-tert-butylcatechol and 4-tert-butylphenol dimer(8).
67.61|A BCF range of 20-88 for p-tert-butylphenol was measured in fish using carp (Cyprinus carpio) which were exposed over an 8-week period(1). The BCF determined in Golden Ide fish (Leuciscus idus melanotus) was 120 over a 30-day exposure(2). According to a classification scheme(3), these BCFs suggest the potential for bioconcentration in aquatic organisms is low to moderate (SRC). A 1-day exposure BCF of 30 was measured in green algae (Chlorella fusca)(2).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of p-tert-butylphenol can be estimated to be 1290(SRC). According to a classification scheme(2), this estimated Koc value suggests that p-tert-butylphenol is expected to have low mobility in soil. The pKa of p-tert-butylphenol is 10.16(3), indicating that this compound will exist almost entirely in the neutral form in the environment(SRC); a small percentage of p-tert-butylphenol may exist in anionic form 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 p-tert-butylphenol has been measured as 1.19X10-6 atm-cu m/mole(1). This Henry's Law constant indicates that p-tert-butylphenol is expected to volatilize from water surfaces(2). 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)(2) is estimated as 38 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 279 days(SRC). p-tert-Butylphenol's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). p-tert-butylphenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.00919 mm Hg(3).
GROUNDWATER: p-tert-Butylphenol was detected in 3 of 4 contaminated groundwater samples collected in Cape Cod, MA in 1996-1997(1).|DRINKING WATER: p-tert-Butylphenol was not detected (MDL of 0.9 ng/L) in various well and tap water samples collected in Cape Cod, MA in 1996-1997(1).|SURFACE WATER: One seawater sample collected near the industrial port of Tarragona, Spain during 2001-2002 contained a p-tert-butylphenol concentration of 0.13 ug/L(1). Analysis of water samples taken the Elbe River and tributaries in 1998 identified p-tert-butylphenol concentrations of 1.4-78 ng/L(2). Water collected from the North Sea in 1998 and 1999 had p-tert-butylphenol concentrations of 0.1-43 ng/L(2). Water collected from the Fujima and Shiratori Rivers (near Lake Biwa, Japan) during 1999-2000 had p-tert-butylphenol concentrations of 0-0.10 and 0-0.02 ng/mL respectively(3). Water from Taihu Lake, China had an average p-tert-butylphenol concentration of 1.26 ppb (range of 0.208-2.32 ppb)(4). Surface water from the Yangtze River, China had p-tert-butylphenol concentrations of 225-1121 ng/L(5).
p-Butylphenol (isomers not specified) was qualitatively detected in cassava volatiles(1).
According to the 2016 TSCA Inventory Update Reporting data, 16 reporting facilities estimate the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of p-tert-butylphenol in the United States may be as low as <10 workers and as high as 100-500; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 97,601 workers (19,779 of these are female) were potentially exposed to p-tert-butylphenol in the US(1). Occupational exposure to p-tert-butylphenol may occur through inhalation and dermal contact with this compound at workplaces where p-tert-butylphenol is produced or used(2). Monitoring and use data indicate that the general population may be exposed to p-tert-butylphenol via inhalation of ambient air and dermal contact with consumer products containing p-tert-butylphenol(SRC). Potential consumer exposure is via use of products with phenolic resins or epoxy resins containing residual p-tert-butylphenol(2). Consumers may be exposed to p-tert-butylphenol in drinking water from drinking water reservoirs coated with epoxy-based paints or from pipelines(2). Consumers may also be exposed to p-tert-butylphenol from polycarbonate used for food contact material(2). p-tert-Butylphenol was identified as a compound that could potentially leach from plastic pipes and contaminate drinking water(3).
Drug Information
Occupational exposure to p-tert-butylphenol (PTBP) was studied in a workplace where workers were engaged in packing this alkylphenol in bags or transporting the bags by fork-lift. The geometrical mean of eight-hour-time-weighted-average (8 hr-TWA) value for personal ambient PTBP level of the packers was 0.39 mg/cu m (n = 15), higher than that of the carriers (0.10 mg/cu m, n = 5). Amounts of PTBP collected in the respirators used by the workers were in proportion to the 8 hr-TWA values but lower than the estimated theoretical amounts; considerable amounts of PTBP were assumed to be absorbed through the respiratory tract. The urine excreted during the latter half of the shift showed the highest levels of PTBP (geometrical mean: packer, 5.07 micrograms/mL, n = 20; carrier, 3.03 micrograms/mL, n = 8). When the workers were away from the workplace, PTBP levels decreased; most was excreted within 24 hr. Correlation between the urinary PTBP levels and 8 hr-TWA values was significant (r = 0.46, n = 19, P less than 0.05), but its extent was weak. The total amounts of urinary PTBP excreted for 24 hr after the start of the shift were two to three times higher than the estimated respiratory absorption of PTBP; PTBP was assumed to be absorbed not only through the respiratory tract but also through intact skin. It was concluded that the personal ambient PTBP level is not a suitable index for personal exposure, and biological monitoring via the PTBP level in the urine excreted at the end of the each shift is useful for the evaluation of personal exposure.|(14)C-labelled p-t-butylphenol (147 ug/kg/day) in Keltrol solution was administered to male Wistar rats by gavage daily for 3 days. Urine and feces were collected daily. 26.7% and 72.9% of the applied dose was eliminated via feces and urine, respectively. Distribution in tissues and organs was as follows: retention in abdominal adipose tissue: not detectable (< 0.01%/g), liver: 0.02%, lung: not detectable (< 0.01%), carcass: 0.1% (data in percent of the applied doses).|Urine samples of workers engaged in packing of p-t-butylphenol (bagging, weighing and sealing of the bags) were collected for 24 hours after the start of each shift. Mean level in urine was 4.20 ug/mL at day shift and 6.12 ug/mL at night shift. In contrast to the urine samples, no free p-tbutylphenol could be detected in sweat collected from the back of workers immediately after bathing.
(14)C-labelled p-t-butylphenol was given intravenously to male Wistar rats at a single dose of 1.2-10.4 mg/kg b.w. and, bile and urine were collected for 4 hours, subsequently. 65-71% and 17-21% of the applied dose were excreted as glucuronide conjugate and sulfate conjugate, respectively (total recovery of radioactivity: 91-93%). The study on incubation of isolated hepatocytes with 3.6-120.2 ug/mL at 37 °C for 1 hour supported the above results concerning the ratio of conjugates and dose-dependency.|[U-(14)C] p-t-butylphenol was given intravenously to rats at a dose of 18 mg/kg b.w. Urine and bile were collected during 24 hours. 1.5 +/- 0.2 umol was excreted as sulfate in the urine, while no significant amounts were found in the biliary excretes. Incubation of 112.65 mg [U-(14)C] p-tbutylphenol with rat liver cytosol at 37 °C for 1 hour yielded 65.5 +/- 11.8 nmol/min/mg protein-1 of sulfated test substance.|4-tert-Butylphenol has known human metabolites that include (2S,3S,4S,5R)-6-(4-tert-butylphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid.
0.13 Days|Workers in a factory with semi-automatization were examined. Non-detectable amounts to traces were found in the urine of plant operators and 1.55-3.34 ug/mL were found in urine of 3 product packers (time averages). The biological half-life of p-t-butylphenol in urine taken from these 3 examinees was calculated to be 4 hr on average.
SYMPTOMS: Irritating to eyes, noses and throat. If inhaled, will cause difficult breathing. ACUTE/CHRONIC HAZARDS: Dangerous when heated to decomposition, emits toxic fumes. (NTP, 1992)
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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. 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)
Fresh air, rest.
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.
Inhalation: Fresh air, rest. Skin: Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention. Eyes: First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. Ingestion: Rinse mouth /SRP: if patient awake alert with good airway protection reflexes./ Rest. Refer for medical attention.|/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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Phenols and related compounds/|/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 necessary. 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 ... . Administer activated charcoal ... . Dilution may be contraindicated because if may increase absorption. Do not use emetics. Cover skin burns with dry, sterile dressings after decontamination ... . Maintain body temperature. /Phenols and related compounds/|/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 ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... Treat seizures with diazepam or lorazepam. ... Use proparacaine hydrochloride to assist eye irrigation ... . /Phenols and related compounds/
/HUMAN EXPOSURE STUDIES/ One data reported that in a routine test series of the North American Contact Dermatitis Group in 1974/75, 1,900 patients with contact dermatitis revealed 1.9% positive reactions and the test series in 1975/76 with 900-2,000 contact dermatitis patients revealed 1.1% positive reactions to 2% of p-t-butylphenol.|/HUMAN EXPOSURE STUDIES/ Ten shoemakers with eczema due to occupational exposure to p-t-butylphenol containing glues were patch-tested for sensitization in 1957. Positive reactions to the glue, its ingredients formaldehyde-p-t-butylphenol resin (50% in ethyl acetate; three patients: 75% in ethyl acetate) and p-t-butylphenol (50% in ethyl acetate) were observed in all patients. After 24 hours, reaction in the p-t-butylphenol test was erythema, edema or papules, and some patients showed a few vesicles. After 48 hours, all patients showed these symptoms.|/HUMAN EXPOSURE STUDIES/ 100 consecutive cases of contact depigmentation due to bindi during a period of 11 months were studied. Bindi adhesive material was found to contain 80% para-tertiary-butylphenol (PTBP), by thin-layer chromatography, infrared spectrophotometry and high-pressure liquid chromatography. The possibility of hypersensitivity to PTBP was ruled out as none of the 15 patients tested with 2% PTBP and 1% para-tertiary-butylphenol-formaldehyde resin gave any positive reactions. Development of depigmentation could have been due either to individual susceptibility or to constant use for a prolonged period. The area of contact being very small, generalized vitiligo as a result of systemic absorption appeared to be a remote possibility.|/CASE REPORTS/ 10 male workers (25-53 years old) occupationally exposed to p-t-butylphenol, formaldehyde and derivatives developed vitiligo 10 months to 7 years after the beginning of their exposure (p-tbutylphenol concentration in dust: 0.12-0.96 mg/cu m air). This symptom occurred especially at the skin of exposed body sites like hands and forearms and consisted of more or less intensively spread finger-nail to palm-sized depigmented spots with irregular configuration. Visible mucous membranes, hair and nails were without any findings. No irritation occurred prior to or during the development of vitiligo. An enlarged liver and spleen was observed in 4 and 1 of these vitiligo patients, respectively. Some liver enzyme activities were increased in two cases, of which one case showed increase in the BSP clearance. In thyroid gland, one patient showed microsomal autoantibodies (titer: 1 : 25600) and thyreoglobuline-auto-antibodies (titer: 1 : 25), and another showed struma diffusa of grade 1 (WHO classification). A stringent combination of vitiligo, hepatosplenopathy and struma could not be found in any patient.|For more Human Toxicity Excerpts (Complete) data for p-tert-Butylphenol (8 total), please visit the HSDB record page.
4-(t-butyl)phenol
The substance can be absorbed into the body by inhalation of its aerosol and through the skin.
Cough. Sore throat.
Redness. Pain.
Redness. Pain.
4-tert-Butylphenol Use and Manufacturing
4-tert-Butylphenol is obtained by reaction of phenol with isobutene at normal or slightly elevated pressure and ca. 80-140 °C in the presence of strongly acidic catalysts such as sulfuric or phosphoric acids, boron trifluoride, activated clays, zeolites or strongly acidic ion-exchange resins. 4-tert-Butylphenol is obtained in ca. 70% yield if tert-butyl phenyl ether is heated to 100 °C in the presence of a clay catalyst that has been activated with sulfuric acid. Silica-alumina (75% SiO2) which has been sintered at 600 °C is said to catalyze isomerizations - trans-alkylations. Mixtures of phenol with 2-tert-butylphenol and 2,4-di-tert-butylphenol give 4-tert-butylphenol at 165 °C. In the industrial process, dehydrated strongly acidic sulfonated polystyrene-polydivinylbenzene ion-exchange resins of the macroporous form are employed which are placed on supporting sieves in columntype reactors. For maximum yields two reactors in series, held at different temperatures, must be used. The first reactor, where the exothermic alkylation takes place ( 90 kJ per mole isobutene reacted), is held at 90-100 °C; the second reactor (isomerization-transalkylation reactor) is held at 120 °C. ... The reactants are introduced to the top of the first reactor in a phenol-isobutene molar ratio of 1.4:1. ... The reaction product leaving the isomerizer is worked up by continuous distillation under reduced pressure (4-10 kPa). ... Product yield is 95 % and product purity is > 98 %.|Catalytic alkylation of phenol with olefins.|Prepared by heating phenol with isobutanol in the presence of zinc chloride.
Phosphate Esters, Fragrances, Oil Field Chemicals-Demulsifiers Polycarbonate Chain Terminator, Glycidyl Ethers Plasticizer for cellulose acetate; intermediate for antioxidants, special starches, oil-soluble phe- nolic resins; pour-point depressors and emulsion breakers for petroleum oils and some plastics; syn- thetic lubricants; insecticides; industrial odorants; motor-oil additives.
Intermediates
Adhesives and sealants
10,000,000 - 50,000,000 lb|Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Phenol, 4-(1,1-dimethylethyl)-:
Adhesive manufacturing|Phenol, 4-(1,1-dimethylethyl)-: ACTIVE
Polycarbonate (PC) plastics find extensive use in baby bottles, food storage containers, and various kitchen items. Possibly hazardous chemicals, bisphenol A (BPA), phenol, p-tert-butylphenol (TBP), and diphenylcarbonate (DPC), are source materials or by-products from PC production. Therefore, a fast and simple analytical method was developed to determine and assess the exposure of BPA, phenol, TBP, and DPC transferred from PC food-contact materials to four different food simulants (water, 4% acetic acid, 50% ethanol, and n-heptane) at different temperatures. The method was validated in terms of limit of detection (LOD) and quantification (LOQ), recovery, and precision for the detection of BPA, phenol, and TBP using HPLC-FLD and of DPC using HPLC-UV. BPA, phenol, TBP, and DPC concentrations transferred from 200 PC samples to food simulants were determined. The highest migration levels of BPA (54.3 ug/L) and phenol (43.8 ug/L) were found in 50% ethanol at 70 °C. TBP did not migrate to any simulant. DPC did not show any migration from PC samples into water and only migrated from a cup to 4% acetic acid at 70 °C and 100 °C, whereas migration occurred from several cups, ladles, spoons, and tongs to 50% ethanol and to n-heptane at 25 °C. Food simulants and temperature were the crucial factors for the migration of BPA and phenol from PC samples. Estimated daily intakes (EDIs), based on food consumption and food-type distribution factors, for BPA, phenol, and DPC were calculated to be 0.007, 0.001, and 2.5X10(-4) ug/kg bw/day, respectively.|We investigated the occurrence of cutaneous depigmentation (vitiligo) among employees of a company that manufactured hydraulic pumps. The interiors of these pumps were injection-molded with rubber. We identified a small but significant cluster of vitiligo cases among a group of employees who frequently handled the rubber used in this injection molding process. Although none of the additives specified in the rubber formulations was a phenolic or catecholic derivative, known to be potential causes of chemically induced vitiligo, gas chromatographic analysis identified a para-substituted phenol (2,4-di-tert-butylphenol, DTBP) in solid samples of the most frequently used rubber. Surface wipe analysis confirmed that workers could be exposed to DTBP from simple handling of the rubber. We subsequently established that the solid bulk rubber used as the base in these stock rubber formulations contained both DTBP and smaller quantities of p-tert-butylphenol. Both had formed as unsuspected byproducts during chemical synthesis of two antioxidants added to the solid bulk rubber by a major rubber supplier. We conclude that the unsuspected presence of potential chemical depigmenting agents in solid bulk rubber, from which industrial rubber products are formulated, may contribute to the occurrence of occupational vitiligo, and that a simple review of ingredients in rubber formulations is inadequate to detect their presence.|We describe the use of gas chromatography with mass spectrometry (GC-MS) in the investigation of a case of allergic contact dermatitis of the lip margins caused by a lip liner. Patch testing identified sensitization to para-tertiary-butylphenol-formaldehyde resin (PTBP-FR), a resin glue frequently used in leather work but rarely found in cosmetics. Investigation specified the para-tertiary-butylphenol (PTBP) component of the resin as the hapten responsible for the allergic contact dermatitis, as well as for associated depigmentation.
Food additives -> Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes|Flavoring Agents -> JECFA Flavorings Index
Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT;
Computed Properties
Molecular Weight:150.22
XLogP3:3.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:150.104465066
Monoisotopic Mass:150.104465066
Topological Polar Surface Area:20.2
Heavy Atom Count:11
Complexity:115
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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