65801-07-2

Upstream product

• 2052-49-5 tetra(n-butyl)ammonium hydroxide 
• 108-95-2 phenol 
• 1392488-21-9 C₆H₅O^(1-)*C₆H₆O*C₂₄H₅₂N⁽¹⁺⁾ 
• 1392488-23-1 C₆H₅O^(1-)*C₆H₆O*C₃₂H₆₈N⁽¹⁺⁾ 
• 1392488-18-4 C₄H₁₂N⁽¹⁺⁾*C₆H₅O^(1-)*C₆H₆O 
• 1392488-19-5 C₆H₅O^(1-)*C₆H₆O*C₈H₂₀N⁽¹⁺⁾ 
• 1643-19-2 tetrabutylammomium bromide 

Downstream Products

• 946-80-5 (benzyloxy)benzene 
• 1643-19-2 tetrabutylammomium bromide 
• 108-95-2 phenol 
• 1392488-20-8 C₆H₅O^(1-)*C₆H₆O*C₁₂H₂₈N⁽¹⁺⁾ 
• 1392488-21-9 C₆H₅O^(1-)*C₆H₆O*C₂₄H₅₂N⁽¹⁺⁾ 
• 1392488-23-1 C₆H₅O^(1-)*C₆H₆O*C₃₂H₆₈N⁽¹⁺⁾ 
• 1392488-19-5 C₆H₅O^(1-)*C₆H₆O*C₈H₂₀N⁽¹⁺⁾ 
• 1126-79-0 n-butyl phenyl ether 

Relevant academic research and scientific papers

Cation-anion CH?O- interactions in the metal-free phenolate, tetra-n-butylammonium phenol-phenolate

Deprotonation of phenol by tetra-n-butylammonium hydroxide and subsequent removal of water by P2O5 results in quantitative formation of tetra-n-butylammonium phenol-phenolate. The compound crystallizes as an ion pair, with the solute phenol molecule intimately attached to the phenolate anion by an O-H?O- hydrogen bond (O?O 2.471(5)?). A short contact between one α-C atom of the tetra-n-butylammonium cation and the phenolate O atom indicates that the ion pair interaction is strengthened by an additional C-H?O- hydrogen-bond, despite the attached phenol.

Effects of charge separation, effective concentration, and aggregate formation on the phase transfer catalyzed alkylation of phenol

The factors that influence the rate of alkylation of phenol under phase transfer catalysis (PTC) have been investigated in detail. Six linear, symmetrical tetraalkylammonium cations, Me4N+, Et 4N+, (n-Pr)4N+, (n-Bu) 4N+, (n-Hex)4N+, and (n-Oct) 4N+, were examined to compare the effects of cationic radius and lipophilicity on the rate of alkylation. Tetraalkylammonium phenoxide·phenol salts were prepared, and their intrinsic reactivity was determined from initial alkylation rates with n-butyl bromide in homogeneous solution. The catalytic activity of the same tetraalkylammonium phenoxides was determined under PTC conditions (under an extraction mechanism) employing quaternary ammonium bromide catalysts. In homogeneous solution the range in reactivity was small (6.8-fold) for Me4N+ to (n-Oct) 4N+. In contrast, under PTC conditions a larger range in reactivity was observed (663-fold). The effective concentration of the tetraalkylammonium phenoxides in the organic phase was identified as the primary factor influencing catalyst activity. Additionally, titration of active phenoxide in the organic phase confirmed the presence of both phenol and potassium phenoxide aggregates with (n-Bu)4N+, (n-Hex)4N+, and (n-Oct)4N+, each with a unique aggregate stoichiometry. The aggregate stoichiometry did not affect the PTC initial alkylation rates.