21566-83-6

Upstream product

• 112-41-4 1-dodecene 
• 108-95-2 phenol 

Relevant academic research and scientific papers

PROCESS FOR PREPARING A PARA-LINEAR ALKYL-SUBSTITUTED HYDROXYAROMATIC COMPOUND

Disclosed herein is a process for preparing an isomeric mixture comprising a major amount of a para-linear mono-alkyl-substituted hydroxyaromatic compound. The process involves the steps of: (a) providing an isomeric mixture comprising a major amount of a para-di(alkyl-substituted)aromatic compound; wherein a first alkyl substituent is a C3 to C8 alkyl moiety and a second alkyl substituent is a C4+n to C8+n linear alkyl moiety, wherein n is 0 to 42 and further wherein the second alkyl substituent is at least one carbon atom greater than the first alkyl substituent; (b) subjecting the isomeric mixture comprising a major amount of a para-di(alkyl-substituted)aromatic compound to oxidation conditions in the presence of an oxygen-containing source, thereby converting the first alkyl substituent which is a C3 to C8 alkyl moiety to a hydroperoxide-containing substituted moiety to produce an isomeric mixture comprising a major amount of a para-linear alkyl-substituted, hydroperoxide-containing substituted aromatic compound; and (c) converting the hydroperoxide-containing substituted moiety to a hydroxyl moiety thereby providing an isomeric mixture comprising a major amount of a para-linear mono-alkyl-substituted hydroxyaromatic compound.

Alkylation of Phenol by 1-Dodecene and 1-Decanol. A Literature Correction

A recent literature report that 1-dodecene reacts with phenol in the presence of sulfated zirconium oxide (superacid), or 1-dodecanol with phenol in the presence of H-Mordenite (zeolite), to afford mostly para-substituted alkylphenols has been shown to be incorrect.The product with zirconium is a mixture of ortho/para isomers (ca. 50-65/50-35), and not the exclusive para isomer as reported.The major product in the case of zeolite catalysis is the o-alkylphenol, with a high degree of end attachment, and not the predominantly claimed para isomers.The selectivity obtained with H-Mordenite during alkylation of phenol differs from the a lkylation of alkylbenzenes and anisole, and is best explained on the basis of a surface catalysis phenomenon.

REACTION OF PHENOL WITH 1-DODECENE IN THE PRESENCE OF ALUMINUM PHENOLATE

The reaction of phenol with 1-dodecene in the presence of aluminum phenolate leads to a mixture of products of the phenol and ether types.The products from orthoalkylation of the phenol predominate, and 2-(3-dodecyl)- and 2-(4-dodecyl)phenols are formed in addition to 2-(2-dodecyl)phenol.