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4-tert-Butylphenol

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4-tert-Butylphenol Basic information
4-tert-Butylphenol Chemical Properties
  • Melting point:96-101 °C(lit.)
  • Boiling point:236-238 °C(lit.)
  • Density 0.908 g/mL at 25 °C(lit.)
  • vapor pressure 1 mm Hg ( 70 °C)
  • FEMA 3918 | P-TERT-BUTYLPHENOL
  • refractive index 1.4787
  • Flash point:113 °C
  • storage temp. room temp
  • solubility ethanol: soluble50mg/mL, clear, colorless
  • form Flakes or Pastilles
  • pka10.23(at 25℃)
  • color White to light beige
  • Specific Gravity0.908
  • PH7 (10g/l, H2O, 20℃)
  • explosive limit0.8-5.3%(V)
  • Water Solubility 8.7 g/L (20 ºC)
  • JECFA Number733
  • Merck 14,1585
  • BRN 1817334
  • Stability:Stable. Incompatible with copper, steel, bases, acid chlorides, acid anhydrides, oxidizing agents.
  • InChIKeyQHPQWRBYOIRBIT-UHFFFAOYSA-N
  • CAS DataBase Reference98-54-4(CAS DataBase Reference)
  • NIST Chemistry ReferencePhenol, p-tert-butyl-(98-54-4)
  • EPA Substance Registry Systemp-tert-Butylphenol (98-54-4)
Safety Information
  • Hazard Codes Xi,N
  • Risk Statements 37/38-41-51/53-62-38-37-34
  • Safety Statements 26-39-61-36/37/39-45
  • RIDADR UN 3077 9/PG 3
  • WGK Germany 2
  • RTECS SJ8925000
  • TSCA Yes
  • HazardClass 8
  • PackingGroup III
  • HS Code 29071900
  • ToxicityLD50 orally in rats: 3.25 ml/kg (Smyth)
MSDS
4-tert-Butylphenol Usage And Synthesis
  • Chemical Properties4-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 polycarbonate are in compact discs, DVD and CD Rom manufacture.
  • OccurrenceReported found in origanum (Coridothymus cap. (L.) Richb.)
  • UsesPhosphate Esters, Fragrances, Oil Field Chemicals-Demulsifiers
  • UsesPolycarbonate Chain Terminator, Glycidyl Ethers
  • UsesPlasticizer 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.
  • PreparationPrepared by heating phenol with isobutanol in the presence of zinc chloride; also from phenol, tert- butyl chloride and excess alkali in alcohol
  • DefinitionChEBI: A member of the class of phenols that is phenol substituted with a tert-butyl group at position 4..
  • General DescriptionCrystals or practically white flakes. Has a disinfectant-like odor. May float or sink in water. Insoluble in water.
  • Air & Water ReactionsInsoluble in water.
  • Reactivity ProfilePhenols, such as 4-tert-Butylphenol, 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 Ka = 1.3 x 10^[-10]). 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.
  • HazardIrritant to eyes and skin.
  • Fire HazardCombustible.
  • Contact allergensPara-tert-butylphenol is used with formaldehyde to produce the polycondensate p-tert-butylphenol-formaldehyde resins (PTBPFR). Major occupational sources are neoprene glues and adhesives in industry, in the shoemaking and leather industries or in car production. It is also used as a box preservative in box and furniture manufacture and in the production of casting molds, car brake linings, insulated electrical cables, adhesives, printing inks, and paper laminates. Para-tertbutylphenol seems to be the sensitizer
  • Safety ProfilePoison by intraperitoneal route. Moderately toxic by skin contact and ingestion. A skin and severe eye irritant. Questionable carcinogen with experimental neoplastigenic data. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid and irritating fumes. See also PHENOL and other butyl phenols.
  • Potential ExposureButylphenols may be used as intermediates in manufacturing varnish and lacquer resins; as a germicidal agent in detergent disinfectants; as a pour point depressant, in motor-oil additives; de-emulsifier for oil; soap-antioxidant, plasticizer, fumigant, and insecticide
  • ShippingUN2430 Alkylphenols, solid, n.o.s. (including C2-C12 homologues), Hazard class: 8; Labels: 8— Corrosive material
  • Purification MethodsCrystallise the phenol to constant melting point from pet ether (b 60-80o). It sublimes in vacuo. Also purify it via the benzoate, as for phenol. The salicylate ester [87-18-30] has m 63-64o (from aqueous EtOH, or EtOH). [Beilstein 6 IV 3296.]
  • IncompatibilitiesVapors may form explosive mixture with air. These phenol/cresol materials can react with oxidizers; reaction may be violent. 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 cause the gas to ignite and explode. Heat is also generated by the acid-base reaction with bases; such heating may initiate polymerization of the organic compound. React with boranes, alkalies, aliphatic amines, amides, nitric acid, sulfuric acid. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). These reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid and can explode when heated. Many phenols form metal salts that may be detonated by mild shock
4-tert-Butylphenol Preparation Products And Raw materials
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