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Home > Encyclopedia > 2-tert-Butylphenol

2-tert-Butylphenol

2-tert-Butylphenol structure

2-tert-Butylphenol 

structure
  • CAS No:

    88-18-6

  • Formula:

    C10H14O

  • Chemical Name:

    2-tert-Butylphenol

  • Synonyms:

    Phenol,2-(1,1-dimethylethyl)-;Phenol,o-tert-butyl-;2-(1,1-Dimethylethyl)phenol;o-tert-Butylphenol;2-tert-Butylphenol;2-tert-Butyl-1-hydroxybenzene;o-t-Butylphenol

  • Categories:

    Organic Chemistry  >  Alcohols, Phenols, Phenol Alcohols

Description

CLEAR LIQUID The butylphenols include several isomers. Solid butylphenols (28805-86-9) generally have properties similar to the above:


Liquid|COLOURLESS-TO-YELLOW LIQUID WITH CHARACTERISTIC ODOUR.


2-tert-Butylphenol is an alkylbenzene.

2-tert-Butylphenol Basic Attributes

150.22

150.22

1907120

201-807-2

NL2FPV3N0Z

1549

3145

DTXSID2026525

LIGHT YELLOW LIQUID|Amber-colored liquid

29071900

Characteristics

20.2

3.3

Liquid

0.9783 g/cm3 @ Temp: 20 °C

-6.8 °C

223 °C @ Press: 760 Torr

>230 °F

1.514

H2O: 0.23 g/100 mL (20 ºC)

Store below +30°C.

0.05 mm Hg ( 20 °C)

Relative vapour density (air = 1): 5.2

Peritoneal-mouse LD50: 82 mg/kg

Thermal decomposition emits spicy and irritating smoke

pKa = 10.28

335 °C

The vapour is heavier than air.

Safety Information

III

8

UN 2922 8/PG 2

2

21/22-23-34-51/53-22

26-36/37/39-45-61

SJ8921000

T,N

The warehouse is ventilated, low-temperature and dry; stored and transported separately from food raw materials, alkalis and oxidants

Stable under normal temperatures and pressures.

P260-P273-P280-P284-P305 + P351 + P338-P310

H302-H311-H314-H330-H400

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.

Combustible. Above 80 °C explosive vapour/air mixtures may be formed.

|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P391, P405, and P501|Aggregated GHS information provided by 76 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302 (99.35%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, 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, P337+P313, P361, P362, P363, P391, P405, and P501|Aggregated GHS information provided by 775 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H227: Combustible liquid [Warning Flammable liquids]|P210, P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P309+P311, P310, P312, P321, P322, P330, P361, P363, P370+P378, P403+P235, P405, and P501

If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Keep run-off water out of sewers and water sources. /Butyl phenols, liquid/

If material not on fire and not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. /Butyl phenols, liquid/|Personnel protection: keep upwind. Avoid breathing vapors. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Avoid bodily contact with the material. /Butyl phenols, liquid/

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable plastic containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Separated from strong oxidants, strong bases, acid anhydrides, acid chlorides, metals and food and feedstuffs.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying.

The substance is corrosive to the skin and eyes. The vapour is irritating to the respiratory tract. Corrosive on ingestion.

NO open flames. Above 80 °C use a closed system and ventilation.

PREVENT GENERATION OF MISTS! IN ALL CASES CONSULT A DOCTOR!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

2-t-Butylphenol was reported in the finished water from an advanced wastewater treatment plant at Lake Tahoe, CA at unreported concentrations(1).

Toxicity

highly toxic

INHIBITORY EFFECTS OF 18 SYNTHETIC PHENOLIC CMPD, ADDED TO DIET, ON BENZO[A]PYRENE-INDUCED NEOPLASIA OF THE FORESTOMACH OF FEMALE MICE WERE DETERMINED. GROUP OF CMPD WITH WEAKER INHIBITORY ACTION INCLUDED 2-TERT-BUTYLPHENOL.

2-t-Butylphenol's production and use as an intermediate in the manufacture of synthetic resins, plasticizers, surface-active agents, and perfumes(1) or as a starting material for antioxidants and agrochemicals(2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1500(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that 2-t-butylphenol will have low mobility in soil(SRC). Limited data, mainly derived by analogy to 4-t-butylphenol, indicate that 2-t-butylphenol may be resistant to biodegradation(SRC). 4-t-Butylphenol (at 30 mg/L) was not biodegraded over a 2 week period using an activated sludge inoculum(4); in river and sea water 4-t-butylphenol showed 11% biodegradation over 3 days(5). However, resting cells of a Pseudomonas strain obtained by selective enrichment with 4-hydroxybenzoate as the sole carbon source, were able to biodegrade 2-t-butylphenol (oxygen uptake rate 26 nmol O2/min/mg protein)(6). Volatilization of 2-t-butylphenol from moist soil surfaces would be slow(SRC) given an estimated Henry's Law constant of 1.4X10-6 atm-cu m/mole(7,SRC).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1500(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that 2-t-butylphenol would adsorb to suspended solids and sediment(SRC) in the water. 2-t-Butylphenol would volatilize slowly from water surfaces based on an estimated Henry's Law constant of 1.4X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated half-lives for a model river and model lake are 31 and 230 days, respectively(3,SRC). An estimated BCF value of 190(3,SRC), from an experimental log Kow(2), suggests that 2-t-butylphenol may bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(5). Limited data, mainly derived by analogy to 4-t-butylphenol, indicate that 2-t-butylphenol may be resistant to biodegradation(SRC). 4-t-Butylphenol (at 30 mg/L) was not biodegraded over a 2 week period using an activated sludge inoculum(6); in river and sea water 4-t-butylphenol showed 11% biodegradation over 3 days(7).|ATMOSPHERIC FATE: According to a suggested classification scheme(1), an experimental vapor pressure of 1.5X10-4 mm Hg at 25 °C(2) indicates that 2-t-butylphenol will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase 2-t-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 about 9.5 hours(3,SRC). Particulate-phase 2-t-butylphenol may be physically removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of 2-t-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,SRC). 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,SRC). 2-t-Butylphenol has a measured pKa of 10.28(2) indicating that this compound will exist mainly in the non-dissociated form at environmental pH's(SRC).

An estimated BCF value of 190 was calculated for 2-t-butylphenol(SRC), using an experimental log Kow of 3.31(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms may be an important fate process(SRC). This compound was rapidly taken up by zebra fish with a steady state concentration reached within 5 hours; the clearance phase required 6 hours(3).

The Koc of 2-t-butylphenol is estimated as approximately 1500(SRC), using an experimental log Kow of 3.31(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this Koc value suggests that 2-t-butylphenol has low mobility in soil(SRC).

The Henry's Law constant for 2-t-butylphenol is estimated as 1.4X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 2-t-butylphenol will volatilize from water surfaces(2,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 31 days(2,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 230 days(2,SRC). 2-t-Butylphenol's estimated Henry's Law constant(1,SRC) indicates that volatilization from moist soil may occur(SRC).

SURFACE WATER: 2-t-Butylphenol was detected in Rhine River water at 2 of 6 sites measured in the Rhine River delta, The Netherlands (concentrations of 0.015-0.022 ug/L)(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 8300 workers (239 of these are female) are potentially exposed to 2-t-butylphenol in the USA(1).

Drug Information

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


Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .


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

MODERATE IRRITANT TO EYES & SKIN.

2-t-butylphenol

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

Cough. Sore throat. Shortness of breath.


Redness. Pain. Burning sensation. Skin burns.


Redness. Pain. Severe deep burns.

2-tert-Butylphenol Use and Manufacturing

Methods of Manufacturing

Isobutylene + phenol (orthoalkylation; coproduced with 2,6-di-t-butylphenol|2-t-Butylphenol is obtained as the main alkylation product if phenol is reacted with isobutene in the presence of sulfonated polystyrene-polydivinylbenzene ion-exchange resins. Reaction of phenol and isobutene in a 1:0.42 molar ratio at 95 °C gives a product mixture. ... 2-t-Butylphenol is obtained in a purity of 99% by distillation. 2-t-Butylphenol is formed with relatively high selectivity by reaction of phenol and isobutene over a gamma aluminum trioxide-catalyst that has been tabletted with 10% graphite and preconditioned by heating to 650 °C in an air stream. ... The selectivity for 2-t-butylphenol is 88% based on phenol conversion.|2-t-Butylphenol is formed with relatively high selectivity by reaction of phenol and isobutene over a gamma aluminum trioxide-catalyst that has been tabletted with 10% graphite and preconditioned by heating to 650 °C in an air stream. ... The selectivity for 2-t-butylphenol is 88% based on phenol conversion.

Uses

Flavors, Fragrances, Insecticides, Phenolic Resins, Antioxidant Intermediate


Flame retardants

All other basic inorganic chemical manufacturing|Phenol, 2-(1,1-dimethylethyl)-: ACTIVE|2-TERT-BUTYLPHENOL WAS PREPARED AND EVALUATED AS INTRAVENOUS ANESTHETIC 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:123
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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