2934-07-8

Usage

Uses

Used in Plastics and Polymers Industry:
2,4,6-Triisopropylphenol is used as an antioxidant and stabilizer for enhancing the durability and resistance of plastics and polymers against degradation, thereby extending their shelf life and performance.
Used in Fuel Industry:
In the fuel industry, 2,4,6-triisopropylphenol serves as a stabilizer to prevent the oxidation and degradation of fuels, ensuring their stability and efficiency during storage and use.
Used in Cosmetics Industry:
2,4,6-Triisopropylphenol is utilized as a UV absorber in cosmetics to protect the skin from harmful ultraviolet radiation, and also for its antimicrobial properties to maintain product integrity and safety.
Used in Personal Care Products:
This chemical is used as an antimicrobial agent in personal care products to prevent the growth of harmful microorganisms, ensuring the cleanliness and safety of these products.
Used in Disinfectants:
2,4,6-Triisopropylphenol is employed in disinfectants for its antimicrobial properties, helping to eliminate bacteria, viruses, and other pathogens in various settings.

InChI:InChI=1/C15H24O/c1-9(2)12-7-13(10(3)4)15(16)14(8-12)11(5)6/h7-11,16H,1-6H3

Upstream product

• 142-82-5 n-heptane 
• 141214-19-9 isopropyl-(2,4,6-triisopropyl-phenyl)-ether 
• 1822-71-5 n-pentylsodium 
• 2741-16-4 isopropoxybenzene 
• 123-31-9 hydroquinone 
• 67-63-0 isopropyl alcohol 
• 108-95-2 phenol 
• 187737-37-7 propene 
• 2934-05-6 2,4-diisopropylphenol 
• 2078-54-8 2,6-diisopropylphenol 
• 143-33-9 sodium cyanide 
• 99-89-8 4-Isopropylphenol 
• 618-45-1 3-isopropylhydroxybenzene 
• 7664-39-3 hydrogen fluoride 

Downstream Products

• 88-69-7 2-(1-methylethyl)phenol 
• 2934-05-6 2,4-diisopropylphenol 
• 2078-54-8 2,6-diisopropylphenol 
• 177793-76-9 ethyl (2,4,6-triisopropylphenoxysulfonyl)acetate 
• 14753-96-9 [2,4,6-tris(1-methylethyl)phenoxy]acetic acid 
• 64532-94-1 isopropyl diphenyl phosphate 
• 55864-04-5 diphenyl-p-isopropylphenyl phosphate 
• 96107-55-0 2,4-diisopropylphenyl diphenyl phosphate 

Relevant academic research and scientific papers

Arene oxidation with malonoyl peroxides

Malonoyl peroxide 7, prepared in a single step from the commercially available diacid, is an effective reagent for the oxidation of aromatics. Reaction of an arene with peroxide 7 at room temperature leads to the corresponding protected phenol which can be unmasked by aminolysis. An ionic mechanism consistent with the experimental findings and supported by isotopic labeling, Hammett analysis, EPR investigations, and reactivity profile studies is proposed.

Highly selective conversion of guaiacol to: Tert -butylphenols in supercritical ethanol over a H2WO4 catalyst

The conversion of guaiacol is examined at 300 °C in supercritical ethanol over a H2WO4 catalyst. Guaiacol is consumed completely, meanwhile, 16.7% aromatic ethers and 80.0% alkylphenols are obtained. Interestingly, tert-butylphenols are produced mainly with a high selectivity of 71.8%, and the overall selectivity of 2,6-di-tert-butylphenol and 2,6-di-tert-butyl-4-ethylphenol is as high as 63.7%. The experimental results indicate that catechol and 2-ethoxyphenol are the intermediates. Meanwhile, the WO3 sites play an important role in the conversion of guaiacol and the Br?nsted acid sites on H2WO4 enhance the conversion and favour a high selectivity of the tert-butylphenols. The recycling tests show that the carbon deposition on the catalyst surface, the dehydration and partial reduction of the catalyst itself are responsible for the decay of the H2WO4 catalyst. Finally, the possible reaction pathways proposed involve the transetherification process and the alkylation process during guaiacol conversion.

Synthesis of phenols and aryl silyl ethers via arylation of complementary hydroxide surrogates

Two transition-metal-free methods to access substituted phenols via the arylation of silanols or hydrogen peroxide with diaryliodonium salts are presented. The complementary reactivity of the two nucleophiles allows synthesis of a broad range of phenols without competing aryne formation, as illustrated by the synthesis of the anesthetic Propofol. Furthermore, silyl-protected phenols can easily be obtained, which are suitable for further transformations.

Method for preparing hydrocarbyl phenol by catalytic conversion of phenolic compound in presence of molybdenum-based catalyst

The invention discloses a method for preparing hydrocarbyl phenol by catalytic conversion of a phenolic compound in the presence of a molybdenum-based catalyst. The method comprises mixing a phenoliccompound, a molybdenum-based catalyst and a reaction solvent, adding the mixture into a sealed reactor, feeding gas into the reactor, heating the mixture to 150-350 DEG C, carrying out stirring for areaction for 0.5-2h, then filtering to remove a solid catalyst and carrying out rotary evaporateion to obtain a liquid product. The phenolic compound has a wide source, a cost is low, product alkyl phenol selectivity is high, an added value is high, alcohol or an alcohol-water mixture is used as a reaction solvent, environmental friendliness is realized, pollution is avoided, any inorganic acids and alkalis are avoided in the reaction process, the common environmental pollution problems in the biomass processing technology are solved, the reaction conditions are mild, the process can be carried out at a low temperature, high-efficiency conversion of the reactants can be realized without consuming hydrogen gas and the method is suitable for large-scale industrial trial production.

Synthesis and catalytic performance of HMCM-49/MCM-41 composite molecular sieve for alkylation of phenol with isopropanol

HMCM-49/MCM-41 composite molecular sieve was synthesized with hydrothermal method. The physicochemical properties of the composite were characterized by using XRD, FT-IR, SEM, N2 isothermal adsorption-desorption and NH3-TPD. Results of different characterizations indicated that the synthesized composite molecular sieve possessed the characteristics of both HMCM-49 and MCM-41. XRD and N2 isothermal adsorption-desorption revealed that it has both micropores and mesopores, a larger surface area than that of HMCM-49, NH3-TPD and pyridine adsorbed FT-IR revealed that the strong acidic sites that caused side reaction in HMCM-49 are deactivated in the composite molecular sieve of HMCM-49/MCM-41. When applied to the alkylation of phenol with isopropanol, the HMCM-49/MCM-41 composite molecular sieve exhibit an enhanced catalytic performance with significant enhancement in p-isopropylphenol and o-isopropylphenol selectivity, which can be ascribed to the composite characteristics of HMCM-49 and MCM-41. This kind of material will has widely industrial application in preparation of alkyl-phenol.

Computational and Experimental Studies of Phthaloyl Peroxide-Mediated Hydroxylation of Arenes Yield a More Reactive Derivative, 4,5-Dichlorophthaloyl Peroxide

The oxidation of arenes by the reagent phthaloyl peroxide provides a new method for the synthesis of phenols. A new, more reactive arene oxidizing reagent, 4,5-dichlorophthaloyl peroxide, computationally predicted and experimentally determined to possess enhanced reactivity, has expanded the scope of the reaction while maintaining a high level of tolerance for diverse functional groups. The reaction proceeds through a novel "reverse-rebound" mechanism with diradical intermediates. Mechanistic insight was achieved through isolation and characterization of minor byproducts, determination of linear free energy correlations, and computational analysis of substituent effects of arenes, each of which provided additional support for the reaction proceeding through the diradical pathway.

CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF

The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.

Continuous-flow synthesis of functionalized phenols by aerobic oxidation of grignard reagents

Phenols are important compounds in chemical industry. An economical and green approach to phenol preparation by the direct oxidation of aryl Grignard reagents using compressed air in continuous gas-liquid segmented flow systems is described. The process tolerates a broad range of functional groups, including oxidation-sensitive functionalities such as alkenes, amines, and thioethers. By integrating a benzyne-mediated in-line generation of arylmagnesium intermediates with the aerobic oxidation, a facile three-step, one-flow process, capable of preparing 2-functionalized phenols in a modular fashion, is established. Putting on airs: Aerobic oxidation of (hetero)aryl Grignard reagents using compressed air proceeds with a gas-liquid continuous-flow system, thus enabling preparation of fucntionalized phenols. By integrating an in-line generation of ArMgBr intermediates with the aerobic oxidation, ortho-functionalized phenols can be assembled. The method demonstrates good functional-group (FG) compatibility, mild reaction conditions, and short reaction times.

A protocol to generate phthaloyl peroxide in flow for the hydroxylation of arenes

A flow protocol for the generation of phthaloyl peroxide has been developed. This process directly yields phthaloyl peroxide in high purity (>95%) and can be used to bypass the need to isolate and recrystallize phthaloyl peroxide, improving upon earlier batch procedures. The flow protocol for the formation of phthaloyl peroxide can be combined with arene hydroxylation reactions and provides a method for the consumption of peroxide as it is generated to minimize the accumulation of large quantities of peroxide.

Metal-free oxidation of aromatic carbon-hydrogen bonds through a reverse-rebound mechanism

Methods for carbon-hydrogen (C-H) bond oxidation have a fundamental role in synthetic organic chemistry, providing functionality that is required in the final target molecule or facilitating subsequent chemical transformations. Several approaches to oxidizing aliphatic C-H bonds have been described, drastically simplifying the synthesis of complex molecules. However, the selective oxidation of aromatic C-H bonds under mild conditions, especially in the context of substituted arenes with diverse functional groups, remains a challenge. The direct hydroxylation of arenes was initially achieved through the use of strong Bronsted or Lewis acids to mediate electrophilic aromatic substitution reactions with super-stoichiometric equivalents of oxidants, significantly limiting the scope of the reaction. Because the products of these reactions are more reactive than the starting materials, over-oxidation is frequently a competitive process. Transition-metal-catalysed C-H oxidation of arenes with or without directing groups has been developed, improving on the acid-mediated process; however, precious metals are required. Here we demonstrate that phthaloyl peroxide functions as a selective oxidant for the transformation of arenes to phenols under mild conditions. Although the reaction proceeds through a radical mechanism, aromatic C-H bonds are selectively oxidized in preference to activated-H bonds. Notably, a wide array of functional groups are compatible with this reaction, and this method is therefore well suited for late-stage transformations of advanced synthetic intermediates. Quantum mechanical calculations indicate that this transformation proceeds through a novel addition-abstraction mechanism, a kind of 'reverse-rebound' mechanism as distinct from the common oxygen-rebound mechanism observed for metal-oxo oxidants. These calculations also identify the origins of the experimentally observed aryl selectivity.