Home > P-cumylphenol > P-cumylphenol(cas:599-64-4)


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599-64-4 Product Description

Chemical Name:P-cumylphenol


CAS NO.:599-64-4

Molecular :C15H16O

Molecular Weight:212.29;

Chemical Properties:

Appearance:White Crytal Powder


Freeaing Point:70-73℃.

Boiling Point:335℃.

Flash Point:160℃.

EINECS: 209-968-0
Index of Refraction: 1.573
IUPAC Name: 4-(2-phenylpropan-2-yl)phenol
Enthalpy of Vaporization: 60.49 kJ/mol
Vapour Pressure: 4.98E-05 mmHg at 25°C

Assay:99% MIN.(GC)


Stability:Stable. Incompatible with oxidizing agents, acid chlorides, acid anhydrides. Combustible.

Use: It can be used forepoxy resin, polycarbonate molecular weight adjustment agent, capping agent; It can be used as a modifier of the phenolic resin, epoxy resin; as antioxidants in plastics, lubricants, rubber products; It can be used in the production of alkylphenol-type non-ionic surfactant; the main application as a pesticide emulsifier; It can also be used for the production of fungicides, disinfectants and other refined products.

Following is the molecular structure of  4-Cumylphenol (599-64-4):
599-64-4 Uses
4-Cumylphenol (599-64-4) is used as surfactant raw materials. Pairs of cumene-based phenol and ethylene oxide addition to be non-ionic surfactant. Fungicides used. The strong anti-mildew product sterilization. Of mineral oil and spindle oil affinity good, Fungicides can be used as lubrication. Compared with the PCP, toxicity is much smaller and does not stimulate the smell, but also can be used for timber sterilization, anti-mildew. Used as a resin raw materials. Made of alkyl phenol and formaldehyde resin, used in coatings, adhesives and so on. The product is also used as a molecular regulator of epoxy resin, reactive diluents, incremental agent; with advanced fatty acids, phosphoric acid esters, etc. produce used plasticizer and stabilizer; also serves as the polycarbonate of molecular weight regulator agent.
599-64-4 Production
4-Cumylphenol (599-64-4) is formed by phenol and alpha methyl styrene condensation. Will join phenol and sulfuric acid, reaction pot, stir cool, alpha methyl styrene. With sodium hydroxide, steamed out not the reaction of phenol and alpha methyl styrene is to use al.were eligible product. Yield is 90%.
599-64-4 Toxicity Data With Reference
orl-frg LD50:335 mg/kg
GTPZAB    Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 12 (12)(1968),44.
Consensus Reports
Reported in EPA TSCA Inventory.

599-64-4 Safety Profile
poison by ingestion. when heated to decomposition it emits acrid smoke and irritating vapors.
safety information of  4-cumylphenol (599-64-4):
hazard codes: xi
xi: irritant
risk statements: 36/37/38
36/37/38: irritating to eyes, respiratory system and skin
safety statements: 24/25-37/39-26
24/25: avoid contact with skin and eyes
37/39: wear suitable gloves and eye/face protection
26: in case of contact with eyes, rinse immediately with plenty of water and seek medical advice
rtecs: sl1942450

Process for preparing p-cumylphenol(cas:599-64-4)
A process for preparing p-cumylphenol(cas:599-64-4) which comprises reacting phenol and methylstyrene in the presence of an inorganic solid acid catalyst having an acid point of an acid strength Ho of up to -3, for example, activated clay and recovering the aimed p-cumylphenol(cas:599-64-4) from the reaction mixture thus obtained by distilling the same while introducing an inert gas such as nitrogen and/or steam into the distillation system is disclosed. The p-cumylphenol(cas:599-64-4) thus obtained has a high purity and an improved color compared with those obtained by conventional methods.

Renal Tubular Cyst Formation in Newborn Rats Treated with p-cumylphenol(cas:599-64-4)
Abstract In this study, we investigated the sequential changes in the development of renal tubular cysts in newborn rats treated with p-cumylphenol(cas:599-64-4) (PCP). Fifteen animals per sex were treated orally with 300 mg/kg/day of PCP for up to 18 days from postnatal day (PND) 4 and were sacrificed on PNDs 8, 12, 19 and 22 and after a 7 day recovery period. On PNDs 8 and 12, slight dilatation of the collecting ducts was frequently observed in the medulla and slight papillary necrosis was also noted in some cases. These dilated collecting ducts were lined with slightly hyperplastic epithelial cells. On PNDs 19 and 22, multiple large cystic changes arising from the collecting ducts in the outer medulla were seen. These cystically dilated ducts were also lined with hyperplastic epithelial cells. During the dosing period, the labeling index of proliferating cell nuclear antigen in the collecting duct epithelium was higher in the PCP-treated group than in the control group at all time points. After a 7 day recovery period, the cystic change still remained, although the cell density was decreased and the epithelial cells became flattened. On the other hand, basophilic tubules with peritubular lymphoid cell infiltration were multifocally observed in the cortex. In conclusion, PCP induced multiple renal cysts that developed in the collecting ducts of the outer medulla in neonatal rats, and it is suggested that epithelial cell proliferation may play some roles in the induction of cystic lesions.

Using p-cumylphenol(cas:599-64-4) and formaldehyde as raw material and solid acid(cation exchange resin) as catalyst,based on orthogonal experiment,a new synthesis technology of p-cumylphenol(cas:599-64-4) formaldehyde resin has been developed through processes such as catalyst condensation,filtration,and distillation etc.The final product is vicious reddle liquid,whose pH is approximate to 7.The product is waterproof,acid-resistant,alkali proof and steady,which is mainly applied to fields such as electrical insulators,paint and rubber product etc.
Liquid Chromatography-mass Spectrometric Analysis of p-cumylphenol(cas:599-64-4) and Bisphenol A in Environmental Waters in Nagoya City
Abstract A highly sensitive analytical method was developed for the determination of para-cumylphenol (PCP) and bisphenol A (BPA) by tandem liquid chromatography-mass spectrometry and was applied to the measurement of environmental water. The method detection limits of PCP and BPA for seawater were 2.2 ng/L and 1.9 ng/L, respectively, and the corresponding values for river water were 5.2 ng/L and 5.0 ng/L. Various water samples in Nagoya city were found to contain PCP and BPA at concentrations ranging from less than 5.2 to 160 ng/L and 33 to 290 ng/L, respectively.

Effect of p-cumylphenol(cas:599-64-4) on the Mold Resistance of Modified Soybean Flour Adhesive and Poplar Plywood

Soy-based adhesive's sensitivity to microbial attack is an aspect that restricts its future application. In an attempt to combat microbial attacks, several preservatives have been evaluated to determine their effects on mold resistance. In this paper, the inhibitory effect of p-cumylphenol(cas:599-64-4) was investigated by observing mold growth on modified soybean-flour adhesives and by evaluating the bonding strength and surface mold growth of bonded poplar plywood. Visual images, scanning electron microscopy, and tensile testing were used. The results showed that the initial microbial attack was delayed and the degree of attack was alleviated because of the preservatives. The bonding strength decreased in samples that contained p-cumylphenol(cas:599-64-4) after the samples were exposed to high humidity. Additionally, no correlation was observed between the degree of microbial growth on the surface of the plywood and amount of the preservatives. These results revealed that it was feasible to incorporate p-cumylphenol(cas:599-64-4) into soy-based adhesives as glue line treatment to improve the mold resistance. Finally, surface treatment of the veneer should be taken into consideration during the plywood manufacturing.

Method and device for producing p-cumylphenol(cas:599-64-4) by rectifying phenol oil tar

The invention relates to a method and device for extracting p-cumylphenol(cas:599-64-4) by taking phenol oil tar generated in a process of synthesizing phenol and acetone through a cumene process and operating a plurality of rectifying towers in series. According to the adoption of the method and the device, the phenol oil tar which pollutes the environment by burning is utilized, and a chemical substance, i.e., cumylphenol with multiples purposes is extracted from the phenol oil tar, so that the aims of changing waste into valuable and lowering the production cost of the p-cumylphenol(cas:599-64-4) are fulfilled.

Brominated p-cumylphenol(cas:599-64-4) flame-retardants for resin composition

Brominated p-cumylphenol(cas:599-64-4) represented by the formula described hereinafter and derivative thereof represented by the formula (2) described hereinabove, process for the preparation of the same, and flame-retardant resin compositions containing the same, are disclosed. Those compounds are useful flame retardant, and can be blended with various thermosetting resins or thermoplastic resins to obtain flame retardant resin compositions.

carboxylation of p-cumylphenol(cas:599-64-4) to 5-cumyl-2-hydroxybenzoic acid

Abstract The purpose of this work was to study carboxylation of alkali metal p-cumylphenol(cas:599-64-4)ates to the corresponding salts of 5-cumyl-2-hydroxybenzoic acid. It has been established by investigations of the effect of cations of alkali metals (lithium, sodium, potassium) on carboxylation of p-cumylphenol(cas:599-64-4) that sodium p-cumylphenolate is carboxylated rapidly and highly selective. It is shown that more than 0. 5% of moisture and 1. 0% of p-cumylphenyl and sodium hydroxide cause the carboxylation parameters to decline. The optimum conditions ensuring maximum yield (94. 8%) of sodium 5-cumyl-2-hydroxybenzoate on the p-cumylphenolate taken have been determined: temperature 150-155 degree C, carbon dioxide pressure 2. 2 MPa, reaction time 140 min.

selective dealkylation of p-cumylphenol(cas:599-64-4) in the presence of cationite
p-Cumylphenol(cas:599-64-4) is a basic component of the so-called phenol resins, which are obtained as a by-product of the cumene method. Interest in the catalytic conversion
of p-Cumylphenol(cas:599-64-4) has increased in recent years in view of the utilization of this resin/i-3/. Its dealkylation to phenol and ~-methylstyrene would seem to be the
most promising procedure.
Calcium and zinc stearates can be successfully used in activating this process/4/.Continuing our investigations of this problem, we now report on a study of the catalytic
conversions of p-Cumylphenol(cas:599-64-4) in the presence of cationite Wofatite OK-80.The initial p-Cumylphenol(cas:599-64-4) had the fol]owing characteristics: b.p. 189-190 ~
(12 Torr); re,p, 72.5-73 ~ lit, /5/: b.p. 190 ~ (12 Tort), m.p. 73-73.5 ~ The Wofatite OK-80 cationite used was a product of the Bitterfeld Co., GDIL The experiments
were carried out in a static apparatus under stirring at 100-140 ~ and at a cationite to p-Cumylphenol(cas:599-64-4) ratio of 1 .' 2. The reaction products were analyzed
chromatographically and spectroscopically. Use wa~ made of the analitical and preparative version of the Carlo Erba and Specord 75 !R apparatus. Carbowax 20 M on
carrier II' SC' 60-80 M was used as stationary phase,Our investigations have shown that the Wofatite OK-80 cationite is reactive against p-Cumylphenol(cas:599-64-4). The main reaction products are phenol and a mixture of isomeric dimers of ~-methylstyrene. Benzene, cumene and ~-methylstyrene were also identified in traces. The conversion of p-Cumylphenol(cas:599-64-4)and the amounts of the main products at 100, 120 and 140 ~ are shown in Fig. 1 (a, b, c), depending on the time of experiment.
The results reveal that in our experimental conditions p-Cumylphenol(cas:599-64-4) is almost completely and selectively dealkylated to phenol and ~-methylstyrene (scheme 1),
which is dimerized to 1.1, 3-trimethyl-3-phenylindane, cis- and trans-2,4-diphenyl--4-methylpentene-2 and 2,4-diphenyl-4-methylpentane-1,
Among the dimeric products, as can be seen from Fig. Id, the dimer with an indane structure is present in the largest quantities, A linear dinner with a trans configuration
is also formed in substantial amounts,The experiment performed with pure a-methylstyrene at 140 oc confirms the   pronounced tendency of this alkenylbenzene ro dimerize in the presence of the cationite used. After 30 rain, ~-methylstyrene is converted into ], i, 3-trimethyl-a-phenylindane (Fig, 2, a), a crystalline product with re,p. 51-52 ~ The changes in the quantities of the isomeric dimers in the first five minutes (Fix. 2,b) of the experiments show

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