Eco-environmental synthesis of vinyl benzoate through transesterification catalyzed by Pd/C catalyst

Abstract

The synthesis of vinyl benzoate via transesterification of vinyl acetate with benzoic acid was investigated by a carbon-supported palladium catalyst. The results showed that Pd (5 wt %)/C catalyst presented good catalytic and reusable performance instead of mercuric salts of strong acids. The conditions of the transesterification reaction for achieving high yields of vinyl benzoate were explored. The optimized conditions are as follows: reaction temperature, 80 o C, reaction time, 10 h, catalyst dosage, 4.0 wt % of reactants, and benzoic acid/vinyl acetate molar ratio, 1:11, respectively, and the yield of vinyl benzoate was 85.7% with the purity of 98.3%. Meanwhile, the prepared Pd/C catalyst could be recycled five times without significant decrease in activity after separating from the product mixture, and the vinyl benzoate yield is still more than 81%. Furthermore, the eco-environmental synthetic method offers great potential for the industrial scale synthesis of vinyl benzoate.

Synthesis of Vinyl Esters of Some Aromatic Carboxylic Acids From Vinyl Acetate

“…Currently, one of the widely used methods for the formation of vinyl esters is the exchange reaction between carboxylic acid and vinyl acetate. The incorporation of the vinyl group of vinyl acetate into aliphatic, aromatic, and heteroaromatic acid is a safe and efficient method of synthesis of vinyl esters [11].…”

Facile synthesis of vinyl esters of aromatic carboxylic acids with participation of 2-chloro-4,6-dimethoxy-1,3,5-triazine

“…Several reports on synthesizing vinyl esters of aliphatic, aromatic, and heteroaromatic acids exist. In the presence of catalysts such as mercury acetate, palladium, ruthenium, rhenium, and other reactions of aliphatic and aromatic acids with acetylene with the formation of corresponding vinyl esters with high yields are carried out; also the synthesis of vinyl esters of carboxylic acids was also carried in the presence of such catalysts as metals complexes and vinyl silanes [8][9][10][11][12][13].…”

Mechanistic aspects of the Pd(OAc)n (n = 1–3) catalyzed ethylene acetoxylation: A density functional theory study

“…However, this process using palladium chloride was limited due to severe corrosion of the equipment by chloride ions. [10,11] Later, Bayer developed a heterogeneous catalyst (Pd-KOAc/Al 2 O 3 ) for the synthesis of vinyl acetate. [12] Similarly, a USI-type heterogeneous catalyst (Pd-Pt-HOAc/Al 2 O 3 ) was developed for the production of vinyl acetate.…”