98-54-4 Usage
Description
Para-tertiary-butylphenol formaldehyde resin (PTBPF-
R) is a polycondensate of para-tertiary-butylphenol
and formaldehyde. Major occupational sources are
neoprene glues and adhesives in industry, in the
shoemaking and leather industry or in car production.
It is also used as a box preservative in box and
furniture manufacture, and in the production of
casting moulds, car-brake linings, insulated electrical
cables, adhesives, printing inks and paper laminates.
Para-tertiary-butyl-phenol is the sensitizer.
Chemical Properties
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 polycarbonate are in compact discs, DVD and CD Rom manufacture.
Occurrence
Reported found in origanum (Coridothymus cap. (L.) Richb.)
Uses
Different sources of media describe the Uses of 98-54-4 differently. You can refer to the following data:
1. Polycarbonate Chain Terminator, Glycidyl Ethers; Phosphate Esters, Fragrances, Oil Field Chemicals-Demulsifiers; Plasticizer for cellulose acetate; intermediate for antioxidants, special starches, oil-soluble phenolic resins; pour-point depressors and emulsion breakers for petroleum oils and some plastics; synthetic lubricants; insecticides; industrial odorants; motor-oil additives.
2. 4-tert-Butylphenol is a phenol derivative. Its contact with skin may lead to leukoderma. It is widely used in the polymer industry. Reaction of 4-tert-Butylphenol with mushroom tyrosinase has been reported to afford 4-t-butyl-o-benzoquinone and kinetics of this enzymatic reaction has been investigated.
3. 4-tert-butylphenol on condensation with formaldehyde gives calix[5]arene which is used in enzyme mimetics.
Application
4-tert-Butylphenol may be employed as carbon and energy supplement in the culture medium of Sphingobium fuliginis strains.4-tert-Butylphenol is suitable reagent used in kinetic study of hydroxylation of 4-tert-butylphenol by mushroom tyrosinase. It may be used in the synthesis of calix[7]arene.
Preparation
Prepared by heating phenol with isobutanol in the presence of zinc chloride; also from phenol, tert- butyl chloride and
excess alkali in alcohol
Definition
ChEBI: 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.
Synthesis Reference(s)
The Journal of Organic Chemistry, 22, p. 988, 1957 DOI: 10.1021/jo01359a609
General Description
Crystals or practically white flakes. Has a disinfectant-like odor. May float or sink in water. Insoluble in water.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Phenols, 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.
Hazard
Irritant to eyes and skin.
Fire Hazard
Combustible.
Contact allergens
Para-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 Profile
Poison 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.
Purification Methods
Crystallise 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.]
Check Digit Verification of cas no
The CAS Registry Mumber 98-54-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 8 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 98-54:
(4*9)+(3*8)+(2*5)+(1*4)=74
74 % 10 = 4
So 98-54-4 is a valid CAS Registry Number.
98-54-4Relevant articles and documents
Efficiency of sulfonic cation-exchange resins used in para-tert-butylphenol production: A comparison based on the kinetics of transalkylation in the phenol-tert-butylphenols system
Voronin,Nesterova,Strelchik,Zhuravskii
, p. 705 - 711 (2014)
The kinetics of transalkylation in the phenol-tert-butylphenols system in the presence of Amberlyst 36 Dry sulfonic cation-exchange resin has been investigated at 353-403 K in the tert-Bu/Ar = 0.10-0.55 mol/mol range. Kinetic characteristics of the o-tert-butylphenol + phenol ai p-tert-butylphenol + phenol (I) and 2,4-di-tert-butylphenol + phenol ai 2p-tert-butylphenol (II) reactions have been determined. The chemical equilibrium in the presence of Amberlyst 36 Dry is reached much sooner than in the presence of KU-23 10/60, a cation-exchange resin used at present. On passing from Amberlyst 36 Dry to KU-23 10/60, the preexponential factor for reaction (I) increases by a factor of 10 and that for reaction (II) increases by a factor of 2000. Thermodynamic characteristics of reaction (I) between 353 and 523 K have been calculated from experimental data and data available from the literature. The thermodynamic characteristics of reaction (II) have been determined experimentally. The enthalpy and entropy of reaction (I) are equal to those of reaction (II). The difference between the equilibrium constants of these reactions is explained. It is recommended that Amberlyst 36 Dry, which proved more efficient than KU-23 10/60, be used in the industrial production of p-tert-butylphenol.
Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes
Ding, Guangni,Fan, Sijie,Wang, Jingyang,Wang, Yu,Wu, Xiaoyu,Xie, Xiaomin,Yang, Liqun,Zhang, Zhaoguo
supporting information, (2021/09/28)
An efficient and mild catalytic deallylation method of aryl allyl ethers is developed, with commercially available Ni(COD)2 as catalyst precursor, simple substituted bipyridine as ligand and air-stable hydrosilanes. The process is compatible with a variety of functional groups and the desired phenol products can be obtained with excellent yields and selectivity. Besides, by detection or isolation of key intermediates, mechanism studies confirm that the deallylation undergoes η3-allylnickel intermediate pathway.
Increasing the steric hindrance around the catalytic core of a self-assembled imine-based non-heme iron catalyst for C-H oxidation
Frateloreto, Federico,Capocasa, Giorgio,Olivo, Giorgio,Abdel Hady, Karim,Sappino, Carla,Di Berto Mancini, Marika,Levi Mortera, Stefano,Lanzalunga, Osvaldo,Di Stefano, Stefano
, p. 537 - 542 (2021/02/09)
Sterically hindered imine-based non-heme complexes4and5rapidly self-assemble in acetonitrile at 25 °C, when the corresponding building blocks are added in solution in the proper ratios. Such complexes are investigated as catalysts for the H2O2oxidation of a series of substrates in order to ascertain the role and the importance of the ligand steric hindrance on the action of the catalytic core1, previously shown to be an efficient catalyst for aliphatic and aromatic C-H bond oxidation. The study reveals a modest dependence of the output of the oxidation reactions on the presence of bulky substituents in the backbone of the catalyst, both in terms of activity and selectivity. This result supports a previously hypothesized catalytic mechanism, which is based on the hemi-lability of the metal complex. In the active form of the catalyst, one of the pyridine arms temporarily leaves the iron centre, freeing up a lot of room for the access of the substrate.
Alkylation of Phenol with tert-Butanol in a Draining-Film Reactor
Maksimov, A. L.,Mel’chakov, I. S.,Terekhov, A. V.,Zanaveskin, L. N.
, p. 569 - 575 (2021/07/26)
The alkylation of phenol with tert-butanol in a displacement draining-film reactor on a heterogeneous catalyst, Beta zeolite, was evaluated. Optimum process conditions ensuring the maximal p-tert-butylphenol yield were determined: phenol:tert-butanol molar ratio (3–3.5):1, superficial liquid velocity 1.0–1.5 m3 m–2 h–1, and temperature 100°C–110°C. A procedure ensuring 100% conversion of tert-butanol and isobutylene (a by-product formed from tert-butanol) was observed.