2,4-Di-tert-pentylphenol

• CAS: 120-95-6
• Catalog Number: ACM120956-1
• Category: Promotional Products
• Molecular Weight: 234.38
• Molecular Formula: C16H26O
• Synonyms: 2,4-Bis(1,1-dimethylpropyl)-pheno
• IUPAC Name: 2,4-bis(2-methylbutan-2-yl)phenol
• SMILES: CCC(C)(C)C1=CC(=C(C=C1)O)C(C)(C)CC
• InChI: InChI=1S/C16H26O/c1-7-15(3,4)12-9-10-14(17)13(11-12)16(5,6)8-2/h9-11,17H,7-8H2,1-6H3
• InChI Key: WMVJWKURWRGJCI-UHFFFAOYSA-N
• Boiling Point: 169-170 °C
• Melting Point: 25 °C
• Flash Point: 113 °C
• Density: 0.93 g/ml
• Appearance: powder to lump to clear liquid

Case Study

High Adsorptive Affinity, Magnetic SPE Compatible and GC Detectable Properties of 2,4-Di-tert-pentylphenol

Komarek K, Safarikova M, Hubka T, et al. Chromatographia, 2009, 69(1/2):133-137.

The adsorptive and chromatographic analytical characteristics of 2,4-Di-tert-pentylphenol (DTP), a typical dialkylphenol endocrine disruptor, were studied via magnetic solid phase extraction (MSPE) water matrix pretreatment and capillary GC-FID quantitative detection experiments. Its dual bulky tert-pentyl branched alkyl substituents endow strong hydrophobic interaction with porous magnetic adsorbents, which is the core structural feature responsible for its high extraction recovery in environmental water samples.
2,4-Di-tert-pentylphenol exhibited prominent hydrophobic adsorptive affinity toward magnetically modified Chromosorb 105 sorbent: Under optimized MSPE parameters (3 min sorption vortex, 0.33 min methanol elution, 3 repeated 1 mL elution cycles) for pH=2 acidified spiked distilled water, DTP achieved 77% extraction recovery, which was 1.6 times higher than short-chain dialkyl analog 2,4-diisopropylphenol (64% recovery) and significantly superior to 2,4-di-tert-butylphenol (70% recovery) under identical experimental conditions. It demonstrated excellent magnetic solid phase extraction compatibility compared with conventional liquid-liquid extraction (LLE): MSPE pretreatment avoided stable emulsion formation commonly observed in LLE when processing turbid biodegradation wastewater matrices; DTP recoveries from tap water via Chromosorb 105 MSPE reached 75.4% with RSD less than 9.2%, while parallel toluene LLE only provided 68.1% recovery with RSD up to 14.7%. Additionally, DTP displayed stable capillary GC-FID detectability with well-resolved chromatographic peaks: Under DB-5HT column temperature program (353 K initial, 283 K/min ramp to 453 K), DTP produced symmetrical sharp chromatographic signals without peak tailing; method limit of detection reached 0.8 μg L⁻¹, falling within the 0.7-1 μg L⁻¹ LOD range suitable for trace alkylphenol monitoring in river and reservoir surface water. Adsorption kinetic curves confirmed DTP's long branched alkyl chains enhance nonpolar van der Waals forces with porous Chromosorb hydrophobic surfaces, enabling rapid saturated adsorption within the first 3 minutes of mixing. These studies demonstrate that 2,4-Di-tert-pentylphenol possesses significant high hydrophobic adsorptive affinity, magnetic solid phase extraction adaptability and stable gas chromatographic quantitative detection properties for environmental water pollution monitoring.
The water sample extraction and chromatographic quantification experiment was split into sorbent screening batches, MSPE parameter optimization groups and real water matrix validation groups. Four magnetic adsorbent materials (Chromosorb 103, Chromosorb 105, Chezacarb B, Chezacarb S) were prepared via iron oxide co-precipitation modification for parallel DTP recovery comparison. MSPE optimization trials adjusted sorption time (0.5-5 min), elution vortex duration (0.33-1 min), single methanol elution volume (0.5-3 mL) and repeated elution times (1-4 cycles) one factor at a time. Test water matrices included spiked distilled water, tap water, Elbe river surface water and NP biodegradation liquid, each split into MSPE experimental subgroup and toluene LLE control subgroup. After solvent evaporation, all extracts were injected into Mega 5160 GC-FID system with DB-5HT capillary column for separation and quantification; external standard calibration curves were established for DTP to calculate extraction recoveries and method LOD values. One-way ANOVA was adopted to analyze recovery differences across sorbents and pretreatment methods at α=0.05 significance threshold. The results verified that DTP's two bulky tert-pentyl alkyl branches strengthen hydrophobic sorbent interaction, making magnetically modified Chromosorb 105 the optimal pretreatment medium for trace DTP analysis in complex environmental water samples.

Steric Hindrance Boosted, Anti-Aggregation and High-Solubility Precursor Properties of 2,4-Di-tert-pentylphenol

Li S, Qi Y, Wang J, et al. ACS Omega, 2024, 9(51): 50774-50785.

The structural modification performance and material precursor functions of 2,4-Di-tert-pentylphenol (DTPP) were studied via DFT geometric simulation, phthalonitrile nucleophilic substitution and zinc phthalocyanine (ZnPc) color film preparation experiments. Its dual bulky tert-pentyl branched alkyl substituents provide superior steric hindrance, which is the core structural characteristic to disrupt π-π stacking and improve organic solubility of ZnPc fluorophores after phenoxy grafting onto phthalocyanine peripheral positions.
2,4-Di-tert-pentylphenol exhibited prominent steric hindrance boosting capacity when grafted as phenoxy side chains on ZnPc rings: DFT geometric optimization showed DTPP-derived C-7 series ZnPcs achieved vertical axial bulkiness up to 9.134-10.480 Å, and substituent-to-isoindole dihedral angles above 80°, which was 12-18° larger than 2,4-di-tert-butylphenol substituted analogs and far higher than short-chain alkoxy modified control ZnPcs; the amplified molecular noncoplanarity effectively weakened intermolecular π-π stacking force between phthalocyanine conjugated planes, eliminating dye aggregation at standard processing concentrations up to 50 μmol/L in PGMEA solvent. It demonstrated outstanding high-solubility precursor activity for synthesizing solution-processable ZnPc dyes: After nucleophilic substitution with chlorophthalonitrile and cyclotetramerization into C-7a/C-7b/C-7c ZnPcs, DTPP-based fluorophores reached solubility of 7.80, 7.87 and 8.40 g per 100 g PGMEA respectively, which were 0.07-0.08 g/100 g higher than corresponding di-tert-butylphenol (C-6) counterparts under identical solvent and temperature conditions; all DTPP-Zn derivatives maintained molar extinction coefficients above 166,760 L·mol⁻¹·cm⁻¹ without sacrificing strong light absorption capacity. Additionally, DTPP-derived ZnPc color films possessed excellent photothermal stability and high light transmittance: Spin-coated polysulfone (PSU) films doped with C-7 series DTPP-ZnPcs showed transmittance over 90% across visible spectrum; after 230 ° constant-temperature baking for 30 min and 365 nm UV light irradiation, the total color difference ΔE remained below 3, meeting industrial color filter standards, while commercial C.I. Pigment Green 7 produced heavy light scattering and transmittance only below 50%. TGA thermal testing verified DTPP-modified ZnPcs had decomposition temperature above 230 °C, with mass loss less than 0.17 wt% after high-temperature thermal treatment. These studies demonstrate that 2,4-Di-tert-pentylphenol possesses significant steric hindrance amplification, phthalocyanine anti-aggregation and high-solubility dye precursor properties for transparent organic color filter materials.
The precursor synthesis and material performance evaluation experiment was divided into DFT simulation batches, nucleophilic substitution synthesis groups and color film characterization groups. For DFT geometric calculation, DTPP and control alkoxy/tert-butyl phenoxy substituents were grafted on three types of chlorinated phthalonitrile skeletons to compute vertical axial bulkiness and molecular dihedral angles via Gaussian 16 Cam-B3LYP method. Synthetic trials reacted DTPP with 4-nitro-, 4,5-dichloro-, tetrachlorophthalonitrile under DMF 80 °C alkaline conditions to produce 7a/7b/7c phthalonitrile intermediates, followed by ZnCl₂ cyclization to obtain target C-7 ZnPc dyes; parallel 2,4-di-tert-butylphenol synthetic control groups were set for solubility comparison. Solubility tests mixed ZnPc powders with PGMEA solvent at 25 °C, saturated solution filtration and vacuum evaporation method was adopted to calculate saturated solubility values. PSU color films were spin-coated at 500 rpm, thermally cured in two stages, then subjected to 230 °C thermal aging and 365 nm LED accelerated light aging; UV-vis transmittance spectrum, TGA thermogravimetry and colorimeter ΔE testing were carried out for all film samples. One-way ANOVA statistical analysis was applied to compare solubility, dihedral angle and transmittance differences of DTPP and control substituted ZnPcs at α=0.05 significance level. The results verified that the two bulky tert-pentyl groups of DTPP deliver stronger three-dimensional steric repulsion than di-tert-butyl analogs, effectively breaking phthalocyanine molecular stacking and preparing high-transmittance, thermally stable transparent color filter dyes.

Custom Reviews

August 02, 2023

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Custom Q&A

What is the chemical formula of 2,4-di-tert-pentylphenol?

The chemical formula of 2,4-di-tert-pentylphenol is C16H26O.

What's the color and shape of 2,4-di-tert-pentylphenol?

2,4-Di-tert-pentylphenol is usually a white or yellowish solid with needle-like or flaky crystals.

What is the purity and melting point of 2,4-di-tert-pentylphenol?

The purity of 2,4-di-tert-pentylphenol is generally above 99%, and its melting point is between 63-66℃.

What is the boiling point and density of 2,4-di-tert-pentylphenol?

2,4-Di-tert-pentylphenol has a boiling point of about 300℃ and a density of about 0.88 g/mL.

What is the antioxidant mechanism of 2,4-di-tert-pentylphenol?

The antioxidant mechanism of 2,4-di-tert-pentylphenol is mainly to capture free radicals and block the transmission of free radical chain reaction, thus inhibiting the oxidation process. It can also react with peroxide or hydroxyl to produce stable products and reduce the formation of oxides.

What is the solubility of 2,4-di-tert-pentylphenol in water?

2,4-Di-tert-pentylphenol is almost insoluble in water, but soluble in organic solvents, such as ethanol, ether, benzene, etc.

What is the application field of 2,4-di-tert-pentylphenol?

2,4-Di-tert-pentylphenol can be used to synthesize additives or stabilizers for various products, such as rubber, plastic, lubricating oil, paint, ink, etc., to improve their heat resistance, light resistance, oxidation resistance, etc.

How is 2,4-di-tert-pentylphenol synthesized?

2,4-Di-tert-pentylphenol can be synthesized by many methods, such as alkylation of phenol with isopentene, alkylation of benzene with isopentene and reoxidation of benzene with isoprene.

What is the antibacterial mechanism of 2,4-di-tert-pentylphenol?

The antibacterial mechanism of 2,4-di-tert-pentylphenol is mainly to destroy the cell membrane of bacteria and interfere with the normal metabolism and growth of cells, thus killing or inhibiting bacteria. It can also interact with bacterial enzymes or protein, affecting its function or structure.

What are the storage conditions of 2,4-di-tert-pentylphenol?

2,4-Di-tert-pentylphenol needs to be stored in a cool and dry place, away from light sources, heat sources and fire sources, and avoid contact with strong oxidants, strong acids, strong bases and other substances.