18254-13-2

Usage

Uses

Used in Rubber and Plastics Industry:
2,4,6-Tris(1-phenylethyl)phenol is used as an antioxidant for rubber, plastics, and other materials to prevent degradation caused by heat and oxygen exposure. Its ability to counteract oxidative stress makes it a valuable additive in these industries, enhancing the durability and stability of the products.
Used in Pharmaceutical Development:
Due to its pharmacological properties, 2,4,6-Tris(1-phenylethyl)phenol has potential applications in the development of new drugs. Its anti-inflammatory and anti-cancer activities suggest that it could be a promising candidate for the treatment of various diseases and conditions. However, further research is needed to fully understand its therapeutic potential and safety profile.
While the compound is generally considered to have low toxicity, there is limited information available on its specific health effects and environmental impact. This warrants further research and evaluation to ensure its safe and responsible use in various applications.

Synthetic route

styrene (292638-84-7) + phenol (108-95-2) → 2-(1-phenylethyl)phenol (4237-44-9) + 2,6-di-(α-methylbenzyl)phenol (4237-28-9) + 2,4-di-(α-methylbenzyl)phenol (2769-94-0) + 2,4,6-tri-(α-methylbenzyl)phenol (18254-13-2)

Conditions	Yield
Stage #1: phenol With aluminium at 140℃; for 1h; Stage #2: styrene at 180 - 190℃; for 5h; Further stages. Further byproducts.;	A 23% B 46% C 8% D 10%

(1-chloroethyl)benzene (672-65-1) + phenol (108-95-2) → 2,4,6-tri-(α-methylbenzyl)phenol (18254-13-2)

Conditions	Yield
at 85 - 130℃;

phenol (108-95-2) + styrene-xylene mixture → 2,4,6-tri-(α-methylbenzyl)phenol (18254-13-2)

Conditions	Yield
With sulfuric acid

styrene (292638-84-7) + phenol (108-95-2) → 2-(1-phenylethyl)phenol (4237-44-9) + 2,6-di-(α-methylbenzyl)phenol (4237-28-9) + 1-(4-hydroxyphenyl)-1-phenylethane (120346-43-2, 1988-89-2) + 2,4-di-(α-methylbenzyl)phenol (2769-94-0) + 2,4,6-tri-(α-methylbenzyl)phenol (18254-13-2)

Conditions	Yield
With sulfuric acid In water at 50 - 200℃; for 3.83333h; Temperature; Autoclave; Inert atmosphere;
With sulfate ion-supported on titanium dioxide at 80℃; for 6h; Reagent/catalyst; Temperature; Inert atmosphere;
With phosphoric acid; sulfuric acid for 3.5h; Heating;
With 5-SO42-/ZrO2 at 100℃; for 6h; Reagent/catalyst; Inert atmosphere;

styrene (292638-84-7) + phenol (108-95-2) → 2,6-di-(α-methylbenzyl)phenol (4237-28-9) + 2,4-di-(α-methylbenzyl)phenol (2769-94-0) + 2,4,6-tri-(α-methylbenzyl)phenol (18254-13-2)

Conditions	Yield
With methanesulfonic acid In neat (no solvent) at 120℃; for 6h; Reagent/catalyst; Overall yield = 100 %Chromat.;
With iron(III) chloride; t-butylsulfonic acid In neat (no solvent) at 120℃; for 6h; Catalytic behavior; Reagent/catalyst; Temperature;

styrene (292638-84-7) + phenol (108-95-2) → 2,4,6-tri-(α-methylbenzyl)phenol (18254-13-2)

Conditions	Yield
With copper(I) bromide In neat (no solvent) at 120℃; for 6h;	65 %Chromat.
With solid catalyst contain with SiO2, AlCl3, NiCl2 at 120℃; for 6h; Inert atmosphere;

Allyl glycidyl ether (106-92-3) + 1,2-epoxytetradecane (3234-28-4) + 2,4,6-tri-(α-methylbenzyl)phenol (18254-13-2) → C49H66O4

Conditions	Yield
Stage #1: 1,2-epoxytetradecane; 2,4,6-tri-(α-methylbenzyl)phenol With potassium methanolate at 120 - 145℃; for 20.1167h; Inert atmosphere; Stage #2: Allyl glycidyl ether for 5h; Inert atmosphere;	98.1%

Allyl glycidyl ether (106-92-3) + 2,4,6-tri-(α-methylbenzyl)phenol (18254-13-2) + Phenyl glycidyl ether (122-60-1) → C45H50O5

Conditions	Yield
Stage #1: 2,4,6-tri-(α-methylbenzyl)phenol; Phenyl glycidyl ether With potassium methanolate at 120℃; for 3.95h; Inert atmosphere; Stage #2: Allyl glycidyl ether for 17.2167h; Inert atmosphere;	97.9%

2,4,6-tri-(α-methylbenzyl)phenol (18254-13-2) + 3-oxa-1,5-dichloropentane (111-44-4) → 1-(2-chloro-ethoxy)-2-[2,4,6-tris-(1-phenyl-ethyl)-phenoxy]-ethane

Conditions	Yield
With sodium hydroxide at 130℃;

2,4,6-tri-(α-methylbenzyl)phenol (18254-13-2) + 3-oxa-1,5-dichloropentane (111-44-4) + aqueous NaOH → 1-(2-chloro-ethoxy)-2-[2,4,6-tris-(1-phenyl-ethyl)-phenoxy]-ethane

Conditions	Yield
at 130℃;

2,4,6-tri-(α-methylbenzyl)phenol (18254-13-2) + aluminium (7429-90-5) + phenol (108-95-2) → 2-(1-phenylethyl)phenol (4237-44-9) + 2,6-di-(α-methylbenzyl)phenol (4237-28-9)

Upstream product

• 672-65-1 (1-chloroethyl)benzene 
• 108-95-2 phenol 
• 100-42-5 styrene 

Downstream Products

• 4237-44-9 2-(1-phenylethyl)phenol 
• 4237-28-9 2,6-di-(α-methylbenzyl)phenol 

Relevant academic research and scientific papers

Optimization of phenol ortho-alkylation with styrene

The results of statistical treatment of experimental data on phenol alkylation with styrene in the presence of aluminum phenoxide as a catalyst are presented. The optimization of the process provides the maximum yield of 2,6-di-α-methylbenzylphenol. The s

Efficient catalyst for hydroarylation reaction of styrene with phenol to obtain high DSP selectivity in mild condition

Background: Technical mixture of styrenated phenols including mono-, di-, and tristyrenated phenol, has been commonly applied for industrial materials such as rubber or plastic stabilizer, antioxidant, and nonionic surfactant, etc. Among these styrenated phenols, di-styrenated phenol should be most effective as rubber and plastic stabilizers. Although a number of catalysts for the synthesis of styrenated phenols have been explored, researches on the synthesis of styrenated phenol generally have been focused on selective preparation of mono-styrenated phenol MSP, rather than distyrenated phenol DSP. In this paper, we have investigated the hydroarylation reaction of styrene with phenol to find the optimal catalyst, including single catalysts and mixed catalysts, to get high selectivity to DSP under mild reaction conditions. Method: Hydroarylation reactions of styrene with phenol using various single catalysts, such as inorganic acids, organic acids, Lewis acids, and metal salt catalysts, have been conducted. To optimize the reaction conditions, hydroarylation reactions of styrene with phenol employing InCl3 catalyst were carried out with a variety of styrene amount, catalyst amount, reaction time, and reaction temperature. Halogenpromoted hydroarylation reactions of styrene with phenol were investigated in the presence of NBS or I2 as a halogen source and a variety of metal halides as a Lewis acid catalyst. Br-promoted hydroarylation reactions of styrene with phenol were accomplished using InCl3 along with NBS under a variety of NBS amount and reaction temperature. To explore the scope of Br-promoted hydroarylation, the reactions of various styrene derivatives with phenol were carried out using NBS and InCl3. Results: Hydroarylation reactions of styrene with phenol using various single catalysts, such as inorganic acids, organic acids, Lewis acids, and metal salt catalysts, have been conducted. Among 19 catalysts used, best results in both high conversion of phenol and high DSP selectivity are obtained with InCl3 catalyst. Using InCl3, total yield of styrenated phenols is 98% and product selectivity MSP/DSP/ TSP is 20/65/13. When InCl3 as an optimal catalyst was applied for the hydroarylation reactions of styrene with phenol under various reaction conditions, the optimal reaction conditions for obtaining a high yield, high DSP, and low MSP are as follows: styrene/phenol = 2 molar ratio, catalyst/phenol = 0.1 molar ratio, reaction time 6 hours, reaction temperature 120°C. In the halogen-promoted hydroarylation reactions of styrene with phenol in the presence of NBS or I2 as a halogen source and various metal halides as a Lewis acid catalyst, best yield (99%) and DSP selectivity (MSP/DSP/ TSP=13/42/41) were obtained using NBS and InCl3. The optimal reaction condition for Br-promoted hydroarylation reaction was found to be phenol 1 eq., styrene 2 eq., InCl3 0.04 eq., NBS 1 eq., 4 hours reaction time, room temperature. For the reactions of various styrene derivatives with phenol using NBS and InCl3, the best DSP selectivity was observed for the CH3-substituted styrene derivative. Conclusion: We have developed hydroarylation reaction of styrene with phenol for obtaining a high yield and a high DSP selectivity even at room temperature. Using NBS as a Br source and InCl3 as a catalyst at room temperature, Br-promoted hydroarylation reaction of styrene with phenol yields good results with respect to both yield and DSP selectivity.

METHOD OF PREPARING FOR SELECTIVE DI-STYRENATED PHENOL USING ZIRCONIUM OXIDE SOLID ACID CATALYST MANUFACTURED BY BEING IMPREGNATED ZIRCONIUM HYDROXIDE IN SULFURIC ACID AQUEOUS SOLUTION

The present invention relates to a selective preparation method of di-styrenated phenol represented by chemical formula 1 obtained by making a phenol compound represented by chemical formula 2 react with a styrene monomer in the presence of a zirconium oxide solid acid catalyst prepared by impregnating zirconium hydroxide with an aqueous sulfuric acid solution. In chemical formulas 1 and 2, R_1 and R_2 are each independently selected from hydrogen, a C_1-C_20 alkyl group, a C_1-C_20 alkoxyl group, a C_3-C_30 cycloalkyl group, and a C_6-C_30 aryl group. The selective preparation method according to the present invention can minimize the amount of an unreacted residual material and can dramatically increase selectivity of di-styrenated phenol by exhibiting a high reactivity in the presence of the zirconium oxide solid acid catalyst prepared by impregnating zirconium hydroxide with the aqueous sulfuric acid solution.COPYRIGHT KIPO 2018

METHOD OF PREPARING FOR SELECTIVE DI-STYRENATED PHENOL USING TITANIUM DIOXIDE SOLID ACID CATALYST

The present invention relates to a method for producing di-styrenated phenol. More specifically, the present invention relates to a method for selectively producing di-styrenated phenol at high yield using solid titanium dioxide acid catalyst. According to the present invention, since the method for producing di-styrenated phenol ensures high reactivity in the presence of solid titanium dioxide acid catalyst, the method for producing di-styrenated phenol can minimize an amount of unreacted residues while remarkably increasing selectivity of di-styrenated phenol.(AA) Titanium dioxide (Powder form, 20 g)(BB) Titanium dioxide + Sulfuric acid + Distilled water (500 ml)(CC) Stir (Room temperature and 3 hours)(DD) Dry (110anddeg;C, and 12 hours)(EE) Sintering (600anddeg;C, 2 hours, and air atmosphere)(FF) Titanium dioxide solid acid catalyst (SO_4^2-/TiO_2) (Sulfuric acid : 5 wt%)COPYRIGHT KIPO 2017

METHOD FOR MANUFACTURING STYRENATED PHENOL

The present invention relates to a method for producing styrenated phenol which is represented by chemical formula 1. According to an embodiment of the present invention, provided is a method for producing styrenated phenol, which comprises the following steps: a step (a) for carrying out a reaction between a phenol compound and a styrene compound in the presence of a first acid catalyst; and a step (b) for carrying out a reaction after additionally inserting a styrene compound into a product obtained in the step (A) in the presence of a second acid catalyst. In the chemical formula 1, n refers to an integer of 1-3.COPYRIGHT KIPO 2017

STYRENATED PHENOLIC COMPOSITION, AND PRODUCTION METHOD THEREFOR

PROBLEM TO BE SOLVED: To provide a styrenated phenolic composition having high content of tristyrenated phenolic compound and low content of impurities such as a styrene oligomer, and a production method therefor. SOLUTION: There are provided the styrenated phenolic composition containing a specific monostyrenated phenolic compound, a specific distyrenated phenolic compound and a specific tristyrenated phenolic compound and the production method for the styrenated phenolic composition. The styrenated phenolic compound has total content of the monostyrenated phenolic compound, the distyrenated phenolic compound and tristyrenated phenolic compound of 98 mass% or more per 100 mass% of an organic product. The content of the tristyrenated phenolic compound in the styrenated phenolic composition is 80 mass% or more and the content of accessory components is 2 mass% or less including 0. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2017,JPOandINPIT