3739-67-1Relevant articles and documents
Kinetic study of synthesizing bisphenol A diallyl ether in a phase-transfer catalytic reaction
Wang, Maw-Ling,Lee, Ze-Fa
, p. 80 - 87 (2006)
In the synthesis of bisphenol A diallyl ether from bisphenol A and allyl bromide, the liquid-liquid mode of operation catalyzed by quaternary ammonium salts was carried out in an alkaline solution/organic solvent two-phase medium. The mono-substituted product was not detected during or after the reaction. In this work, a rational reaction mechanism is proposed and a kinetic model then established. The apparent rate constant of the organic-phase reaction was obtained from experimental data. The effects of the reaction conditions, including agitation speed, organic solvents, quaternary ammonium salts, inorganic salts, temperature, alkali compounds, amount of potassium hydroxide, and water on the conversion of allyl bromide, were investigated in detail. The presence of a small amount of tetrabutylammonium bromide (TBAB) in the chlorobenzene/water system produced a rate over several folds larger than that of the reaction system in the absence of phase-transfer catalyst. The presence of alkali compounds promoted the formation of alkoxide and enhanced the extractive efficiency due to the salting out effect. The present etherification via phase-transfer catalyst could operate at lower temperatures to avoid Claisen rearrangement, which usually occurs at higher temperatures. Rational reasons to account for the absence of mono-substituted product are explained satisfactorily. Peculiar phenomena in investigating the effects of the volume of organic solvent, amount of KOH, and the volume of water and alkali compounds on the apparent rate constants are also explained.
Process for synthesizing diallyl phenol ether compound through azeotropic dehydration
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Paragraph 0025-0026, (2021/01/04)
The invention discloses a process for synthesizing a diallyl phenol ether compound by azeotropic dehydration, which comprises the following steps: (1) dissolving a bisphenol compound in an organic solvent, and adding an inorganic base or an aqueous solution of the inorganic base to react to generate phenolate; and (2) vacuumizing the mixture obtained by the reaction in the step (1) or adding a water-carrying agent for dehydration, adding an allyl compound after dehydration is finished, and reacting to obtain the diallyl phenol ether compound. The invention provides a method for preparing a bisphenol compound into an intermediate product phenate and then reacting the intermediate product phenate with a propenyl compound to generate a diallyl phenol ether compound product, which comprises the following steps: adding a water-carrying agent or vacuumizing to remove water in a reaction system; according to the method, the problem of raw material waste caused by hydrolysis of propylene compounds can be effectively avoided, the reaction yield and purity are improved, aftertreatment is simple, and economic benefits are improved.
Pd-catalyzed substitution of the oh group of nonderivatized allylic alcohols by phenols
Rukkijakan, Thanya,Akkarasamiyo, Sunisa,Sawadjoon, Supaporn,Samec, Joseph S. M.
, p. 4099 - 4104 (2018/04/14)
Nonactivated phenols have been employed as nucleophiles in the allylation of nonderivatized allylic alcohols to generate allylated phenolic ethers with water as the only byproduct. A Pd[BiPhePhos] catalyst was found to be reactive to give the O-allylated phenols in good to excellent yields in the presence of molecular sieves. The reactions are chemoselective in which the kinetically favored O-allylated products are formed exclusively over the thermodynamically favored C-allylated products.