140-66-9 Usage
Chemical Properties
white powder
Uses
4-tert-Octylphenol (4t-OP) is used in manufacturing processes as an intermediate in the generation of surfactants, synthetic rubber additives, or resins. 4t-OP is also used to manufacture alkylphenol ethoxylates. It is found mainly in detergents, cleaning products, and emulsifiers and less frequently in paints, personal care products, pesticides, paper, pulp, and textiles.
General Description
4-tert-Octylphenol is a potential environmental pollutant and it exhibits toxic and estrogenic effects on mammalian cells. It binds to estrogen receptors and exerts estrogenic actions in vitro. The transformation of the 4-tert-octylphenol upon irradiation at 253.7nm and by hydroxyl radicals generated by the photolysis (λexc = 253.7nm) of hydrogen peroxide in aqueous solution has been studied.
Health effects
4-tert-octylphenol (OP) is an endocrine-disrupting chemical that causes harmful effects to human health.a common environmental pollutant showing weak estrogenic effects. 4-tert-Octylphenol has been shown to cause harm to the male reproductive system of vertebrates.High doses of several alkylphenols, including 4- tert-octylphenol, have altered estrogenic effects, including sex hormone levels, estrus cycles, reproductive outcomes, neonatal sexual development, as well as impaired production of steroid hormone and testicular atrophy.
Environmental Fate
Studies have shown that 4t-OP will adsorb to sediments.
Purification Methods
Crystallise the phenol from n-hexane and/or distil it in a vacuum. [Beilstein 6 III 2051, 6 IV 3484.]
Toxicity evaluation
4t-OP has been shown to be an estrogen receptor (ER) agonist.
Estrogenic effects of 4t-OP have been demonstrated in human
cells, with 4t-OP displacing the natural estrogen 17b estradiol
from its receptor, and 4t-OP inducing cell proliferation in
estrogen-dependent cell proliferation assays. In vivo confirmation
of 4t-OP’s estrogenicity has been confirmed with the uterotrophic
assay.
Check Digit Verification of cas no
The CAS Registry Mumber 140-66-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 0 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 140-66:
(5*1)+(4*4)+(3*0)+(2*6)+(1*6)=39
39 % 10 = 9
So 140-66-9 is a valid CAS Registry Number.
InChI:InChI=1/C14H22O/c1-2-3-4-5-6-7-8-13-9-11-14(15)12-10-13/h9-12,15H,2-8H2,1H3
140-66-9Relevant articles and documents
-
Simons,Archer
, p. 451 (1940)
-
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.
Chloroindate(iii) ionic liquids as catalysts for alkylation of phenols and catechol with alkenes
Gunaratne, H. Q. Nimal,Lotz, Tobias J.,Seddon, Kenneth R.
scheme or table, p. 1821 - 1824 (2011/01/07)
Chloroindate(iii) ionic liquids are shown to be versatile catalysts for the alkylation of phenols with alkenes, giving high conversions to alkylated phenols with high selectivities.
Synthesis of 4-tert-octylphenol and 4-cumylphenol by metal triflate and metal triflimidate catalysts
Le Rouzo, Guillaume,Morel-Grepet, Marielle,Simonato, Jean-Pierre
, p. 521 - 522 (2007/10/03)
Metal inflates and metal triflimidates are shown to catalyse efficiently the Friedel-Crafts alkylation of phenol with alkenes. Bismuth, copper and scandium triflates lead to very good yields with excellent para-selectivities.
