styrenated phenol

• CAS: 61788-44-1
• Catalog Number: ACM61788441
• Category: Main Products
• Molecular Weight: 406.56
• Molecular Formula: C30H30O
• Synonyms: Styrenatedphenols
• Appearance: Light yellow viscous liquid
• Application: Styrenated phenol, known as MSP, has a high mono ratio of 75%. This product, also referred to as Tri-Styrylphenol, has multifunctional applications that vary depending on the mono/para ratio.

Case Study

Styrenated phenol improves natural rubber properties

Dileep, P., and Sunil K. Narayanankutty. Polymer Testing 82 (2020): 106302.

The effects of nanosilica on the cure, mechanical properties, thermal properties, dynamic mechanical properties and barrier properties of natural rubber vulcanizates containing antioxidant styrenated phenol were studied. In addition, the effect of antioxidant modified silica on the overall properties of natural rubber was studied. In addition, the aging properties of the composites were studied to evaluate the effect of modified nanosilica on natural rubber.
The Mooney viscosity (ML 1+4 @ 100 °C) of natural rubber is 70±2 and the density is 0.94 g/cm3. Nanosilica and modified nanosilica with a surface area of 575 m2/g were prepared. Mixing was carried out at 60 rpm at 70 °C for 8 min in an internal mixer equipped with Banbury rotors. The natural rubber was masticated for 3 min and ZnO, stearic acid and styrenated phenol were added, followed by nanosilica and DEG. After another 3 min, CBS, TMTD and sulfur were added. Mixing was continued for 2 minutes to distribute all ingredients evenly. After mixing, the compound was removed from the mixing chamber and rolled out five times in a laboratory two-roll mixer (size 6"x12") with tight roll gaps and a final roll gap of 3 mm. The compound was stored at room temperature for 24 hours for maturation before molding. The compound was cured in a standard mold at 150°C for the optimum cure time using an electrically heated hydraulic press with a platen size of 12"x12".

Study on the catalytic synthesis of styrenated phenol

Lee, Seungmin, et al. Journal of Nanoscience and Nanotechnology 18.2 (2018): 1461-1464.

Styrenated phenol was prepared by alkylation of phenol using silica-supported NiCl2 and AlCl3. The conversion of phenol and styrene and the selectivity of styrenated phenol in the alkylation reaction were studied. With the catalyst supported by Al·Ni/SiO2, the conversion of phenol was almost 100%. The product was in the form of a mixture of monostyrenated phenol, distyrenated phenol, and tristyrenated phenol. The selectivity of styrenated phenol varies depending on the reaction conditions. In this study, a catalyst containing SiO2, NiCl2, and AlCl3 was used to carry out the SP reaction by adjusting the reaction temperature, reaction time, catalyst dosage, catalyst composition, and the maximum value of styrene dosage, and the DSP selectivity conditions were found. The reactants and products were analyzed using GC. With the increase of reaction temperature, the selectivity of DSP and the conversion of reactants were higher, but the reaction did not proceed at 130°C. With the increase of reaction time, the conversion of reactants and the selectivity of DSP increased, but did not change after 10 hours. As the amount of catalyst increases, the conversion of the reactants increases, but the selectivity of DSP tends to decrease. When the amount of styrene is 2.5eq, the reactant conversion and DSP selectivity are the highest. When the equivalent is 2.0 eq, the selectivity of MSP increases. As the equivalent increases, the selectivity of TSP gradually increases. As the amount of catalyst AlCl3 increases, the conversion of the reactants is higher, but the selectivity of DSP is the highest at 3 g. This trend was not observed in the experiments depending on the amount of NiCl2 in the catalyst. It is believed that the AlCl3 and NiCl2 catalysts should have a specific ratio to be active.
The catalyst was prepared by impregnating SiO2 (5 g) with an aqueous solution of NiCl2·6HO (1 g) and AlCl3·6HO (3 g) for 3 h. It was then vacuum dried at 150°C for 6 h and calcined at 300°C for 6 h. The catalyst was stored in a desiccator until use. Phenol (25 mmol, 2.3528 g) and Al·Ni/SiO2 (3 wt%, 0.2659 g) were added to a flask. The mixture was stirred at 60°C for 30 minutes, and then styrene (62.5 mmol, 6.5094 g) was added. After stirring at 120°C for 10 hours, the reaction mixture was separated from the catalyst and the product using a filter. The separated product was analyzed by GC.

Alternative catalysts for alkylation based on styrenated phenol

Malshe, V. C., and E. S. Sujatha. Reactive and Functional Polymers 43.1-2 (2000): 183-194.

Conventional cation exchange resin catalysts used for phenylxylene ethane (PXE) synthesis were found to deactivate after a few cycles. The determination of the residual double bond concentration of styrene-divinylphenyl ion exchange resin catalysts was investigated. Indion-130 and Amberlyst-15 have bromine numbers of 6-7. An alternative catalyst based on styrenated phenol and formaldehyde was developed that does not use conventional vinyl chemistry to form the polymer. PXE synthesis was explored using these new catalysts. Improved catalyst performance in PXE synthesis was achieved compared to conventional catalysts. The reusability and temperature stability of the new catalysts were verified by the esterification of phthalic anhydride with 2-ethylhexanol.
Polycondensation of trihydroxymethylphenol with styrene-substituted phenol on a silica gel support. Styrenated phenol and hydroxymethylphenol were mixed in a 3:2 ratio with oxalic acid catalyst. The total solids content of the mixture was 40%. The mixture was diluted with methanol to obtain a 20% solution. The solution was loaded onto silica gel, excess methanol was evaporated, and polymerized at 423 K for 4 h, followed by post-curing at 473 K for 5 h. The polymerized product was sulfonated with chlorosulfonic acid in dichloroethane solvent at 353 K for 4 h. The molar ratio of polymer to acid was 1:2. After sulfonation, the excess acid was washed with sulfuric acid of decreasing concentration to avoid cracking, and finally washed with distilled water.

Catalytic reaction to produce styrenated phenols

Kim, Vicna, et al. Rapid Communication in Photoscience 5.1 (2016): 13-15.

The reaction of styrene with phenol to produce styrenated phenols in the presence of photoacid catalysts was studied. Under 450 nm light irradiation, the protonated merocyanine photoacid is converted to the spiropyran form and releases a proton. The reaction of styrene with phenol was carried out at room temperature using merocyanine photoacid catalyst under 450 nm light irradiation and compared with the results obtained at a reaction temperature of 120 °C using some selected catalysts. Styrenated phenols are typical hindered phenols. Styrenated phenol derivatives or related hydroarylation products obtained from the reaction of styrene derivatives with phenol or aromatic hydrocarbons are very important as antioxidants and in chemical industries such as fine chemicals, bulk chemicals, pharmaceuticals and agrochemicals. Styrenated phenols are prepared by the acid-catalyzed reaction of phenol and styrene using Lewis acid catalysts, inorganic protic acids or organic protic acid catalysts.
In order to compare the effect of photoacid with common protic acids or Lewis acids on the catalytic reaction of phenol with styrenated acid, photoacid MCH, protic acid catalyst H2SO4 or Lewis acid FeCl3 were used as acid catalysts. When using H2SO4 or FeCl3, the reaction of styrene and phenol was carried out under the following reaction conditions: reaction temperature was 120°C, reaction time was 6 hours, no solvent was added to the reaction mixture, the reactant molar ratio was styrene/phenol = 2/1, and the amount of catalyst was 0.1 mol/1 mol phenol. The reaction using the photoacid MCH was carried out under 450nm light irradiation, using the same reaction conditions as above, except that a solvent (acetonitrile/water = 7/3) was used and the reaction was carried out at room temperature.