5892-47-7

Usage

Uses

Used in Polymer and Plastics Industry:
2,4,6-tri-sec-butylphenol is used as an antioxidant and stabilizer for enhancing the resistance of polymers, resins, and plastics to degradation and deterioration caused by heat, oxygen, and light.
Used in Lubricants and Oils Industry:
2,4,6-tri-sec-butylphenol is used as an additive in lubricants, oils, and fuels to improve their oxidative stability and extend their shelf life.
Environmental and Health Concerns:
Despite its widespread industrial applications, 2,4,6-tri-sec-butylphenol has raised concerns due to its potential environmental persistence and possible toxic effects on aquatic organisms. Ongoing research and regulation efforts are focused on monitoring and mitigating the associated risks.

InChI:InChI=1/C18H30O/c1-7-12(4)15-10-16(13(5)8-2)18(19)17(11-15)14(6)9-3/h10-14,19H,7-9H2,1-6H3

Synthetic route

4-sec-Butyl-2,6-bis-(1-methyl-allyl)-phenol (101886-62-8) → 2,4,6-tri-(sec-butyl)phenol (5892-47-7)

Conditions	Yield
With palladium on activated charcoal; ethanol Hydrogenation;

2-sec-butylphenol (89-72-5) + 2,4-di-(sec-butyl)phenol (1849-18-9) → 2,4,6-tri-(sec-butyl)phenol (5892-47-7) + phenol (108-95-2)

Conditions	Yield
Al(Hal)3 at 169.9℃; for 24h; Equilibrium constant; Thermodynamic data; var. temp., time, ΔrH0m, ΔrS0m;

butan-1-ol (71-36-3) + phenol (108-95-2) → 2-sec-butylphenol (89-72-5) + 4-(1-methylpropyl)phenol (99-71-8) + n-butyl phenyl ether (1126-79-0) + 2,4-di-(sec-butyl)phenol (1849-18-9) + 2,6-di-sec-butylphenol (5510-99-6) + 2,4,6-tri-(sec-butyl)phenol (5892-47-7)

Conditions	Yield
multistep reaction; alkylation of phenol in the presence of KU-23 sulfonated cation-exchanger;

aluminium trichloride (7446-70-0) + but-2-yl phenyl ether (10574-17-1) → 1-(2-methylpropyl)phenol (3522-86-9) + 2,4,6-tri-(sec-butyl)phenol (5892-47-7)

4-sec-Butyl-2-(1-methyl-allyl)-phenol (107771-33-5) → 2,4,6-tri-(sec-butyl)phenol (5892-47-7)

Conditions	Yield
Multi-step reaction with 3 steps 2: N,N-diethyl-aniline 3: palladium/charcoal; ethanol / Hydrogenation View Scheme

but-2-enyl-[4-sec-butyl-2-(1-methyl-allyl)-phenyl]-ether (109068-15-7) → 2,4,6-tri-(sec-butyl)phenol (5892-47-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-diethyl-aniline 2: palladium/charcoal; ethanol / Hydrogenation View Scheme

2,4,6-tri-(sec-butyl)phenol (5892-47-7) + phenol (108-95-2) → 2-sec-butylphenol (89-72-5) + 2,4-di-(sec-butyl)phenol (1849-18-9)

Conditions	Yield
Al(Hal)3 at 169.9℃; for 24h; Equilibrium constant; Thermodynamic data; var. temp., time, ΔrH0m, ΔrS0m;

Upstream product

• 89-72-5 2-sec-butylphenol 
• 1849-18-9 2,4-di-(sec-butyl)phenol 
• 71-36-3 butan-1-ol 
• 108-95-2 phenol 
• 109068-15-7 but-2-enyl-[4-sec-butyl-2-(1-methyl-allyl)-phenyl]-ether 
• 107771-33-5 4-sec-Butyl-2-(1-methyl-allyl)-phenol 
• 101886-62-8 4-sec-Butyl-2,6-bis-(1-methyl-allyl)-phenol 
• 7446-70-0 aluminium trichloride 
• 10574-17-1 but-2-yl phenyl ether 

Downstream Products

• 89-72-5 2-sec-butylphenol 
• 1849-18-9 2,4-di-(sec-butyl)phenol 

Relevant academic research and scientific papers

Equilibria for the isomerization of (secondary-alkyl)phenols and cyclohexylphenols

Equilibria of a series of isomerizations and trans-alkylations of alkylphenols have been investigated in the liquid phase over a wide range of temperatures.Equilibria of isomerizations connected with the displacement of a substituent on a benzene nucleus were studied for secondary-butyl, -amyl, -hexyl, and cyclohexyl-phenols, and di-(secondary-butyl)phenols.Equilibria of positional isomerization connected with the displacement of an oxyphenyl radical in an alkyl chain were investigated for oxyphenyl-pentanes, -hexanes, -octanes, and -decanes.Trans-alkylation was investigated for di- and tri-(secondary-butyl)phenols.Values of ΔrH0m and ΔrS0m were found for all investigated reactions.An analysis was made of the thermodynamic quantities for the reactions.Enthalpies of formation of isopropylphenols (IPP) in the gaseous state were calculated.The values of ΔfH0m/(kJ * mol-1) were found at 298.15 K: o-IPP, -(175.3 +/- 2.4); p-IPP, -(175.3 +/- 2.4); m-IPP, -(175.3 +/-2.4); 2,4-di-IPP, -(254.1 +/- 2.8); 2,5-di-IPP, -(254.1 +/- 2.8); 2,6-di-IPP, -(254.1 +/- 2.8); 3,5-di-IPP, -(254.1 +/- 2.8); 2,4,6-tri-IPP, -(333.0 +/- 3.1).

Phenol transalkylation process

Phenols having an unsubstituted ortho position are transalkylated in the ortho position by mixing them with an ortho-alpha-branched alkylphenol (e.g., 2,6-di-sec-butylphenol) and an aluminum phenoxide catalyst and heating the mixture to 100°-350°C., preferably in a closed system and in the presence of olefin corresponding in structure to the ortho-alpha-branched alkyl group.