2769-94-0

Usage

Appearance

White, crystalline solid

Solubility

Insoluble in water, soluble in organic solvents

Common uses

Antioxidant, stabilizer, and UV absorber in plastics, rubber, and other industrial materials; ingredient in personal care products like sunscreen

UV protection

Protects against harmful UV radiation

Safety precautions

Handle with care and follow safety guidelines to minimize potential health and environmental hazards

InChI:InChI=1/C22H22O/c1-16(18-9-5-3-6-10-18)20-13-14-22(23)21(15-20)17(2)19-11-7-4-8-12-19/h3-17,23H,1-2H3

Upstream product

• 100-42-5 styrene 
• 108-95-2 phenol 
• 4237-44-9 2-(1-phenylethyl)phenol 

Relevant academic research and scientific papers

Occurrence and estrogenicity of phenolics in paper-recycling process water: Pollutants originating from thermal paper in waste paper

Eight phenolics were detected in samples collected from areas where paper-recycling process water is discharged. The detected concentration levels were up to 270 μg/L and 230 μg/g in water samples and sediment samples, respectively, obtained from both the outfall of the paper-recycling process water and its downstream areas. In particular, totarol (compound 4), 2,4-bis(1-phenylethyl)phenol (compound 6), 4,4′-butylidenebis(6-t-butyl-m- cresol) (compound 7), 2,4-bis(1-phenylethyl)-6-chlorophenol (compound 8), and 4-hydroxy-4′-isopropoxydiphenyl sulfone (compound 9) were identified for the first time as environmental pollutants. The estrogenicities of the identified compounds were assessed by yeast two-hybrid assays incorporating either the human or medaka fish (Oryzias latipes) estrogen receptor α (hERα and medERα, respectively) and an estrogen receptor competitive enzyme-linked immunosorbent assay (ER-ELISA) both with and without metabolic activation by a rat liver S9 mix. Bisphenol A (compound 3) and 2-naphthol (compound 1) exhibited activity in the assays of both hERα and medERα without the S9 mix. The relative activity (%) to 17β-estradiol was 0.0015% for compound 3 and 0.0009% for compound 1 in the hERα assay and 0.027% for compound 3 and 0.0093% for compound 1 in the medERα assay. These compounds were attenuated by the S9 mix. The binding affinity was evaluated using an ER-ELISA. Compounds 3, 4, 6, and 7 exhibited affinity without the S9 mix. After exposure to the S9 mix, however, the binding affinity of compound 7 was eliminated by the S9 mix; those of compounds 3, 4, and 6 were attenuated; and that of compound 8 exhibited affinity. A comprehensive assessment of the estrogenicities of the phenolics originating from thermal paper and their implications for an aquatic environment may require an examination of the components of the phenolics, as in the present study.

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

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 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

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

Selective process for preparting 2,4- or 3,6-di-substituted phenol compounds

A selective process for preparing a 2,4- or 3,6-di-substituted phenol compound which comprises reacting an olefin compound of the formula: STR1 wherein R1 is hydrogen, halogen, alkyl, halogen substituted alkyl, aryl, halogen substituted-aryl or alkyl substituted-aryl; and R2, R3 and R4 are the same or different and each is hydrogen, halogen, alkyl, halogen substituted-alkyl or aralkyl; with a phenol compound of the formula: STR2 wherein R5 is hydrogen, hydroxy, halogen, alkyl, halogen substituted-alkyl, alkoxy or --C(R6)(R7)CH(R8)(R9) (wherein R6 is hydrogen, halogen, alkyl, halogen substituted-alkyl, aryl, halogen substituted-aryl or alkyl substituted-aryl; and R7, R8 and R9 are the same or different and each is hydrogen, halogen, alkyl, halogen substituted-alkyl or aralkyl), in the presence of a phosphorus compound and a carboxylic acid compound as catalysts. The methods of the present invention, which is used a phosphorus compound and a carboxylic acid compound as catalysts, are enable to make the separation procedures easy, make the reaction process and time short, not to produce any colored resultant product, and reduce that cost in manufacturing procedures.

REACTIVITY OF 2,4- AND 2,6-DIALKYLPHENOLS DURING SUBSTITUTION BY WEAK ELECTROPHILIC AGENTS

The 2,4- and 2,6-dialkylphenols have different reactivities during substitution by weak electrophiles. 2,4-Dialkylphenols enter readily into acid-catalyzed alkylation and condensation with aldehydes, and their reactivity is practically independent of the structure of the alkyl substituents. 2,6-Dialkylphenols have significantly lower reactivity in these reactions, while sterically hindered 2,6-dialkylphenols hardly react at all with alkenes and aldehydes under the conditions of acid catalysis.This is evidently due to weakening of the interaction between the hydroxyl group and the aromatic ring in the conjugation mechanism.