32747-57-2

Upstream product

• 98-83-9 isopropenylbenzene 

Downstream Products

• 98-86-2 acetophenone 
• 193805-51-5 3-Methyl-3-phenyl-1,2,4-trioxaspiro[5.4]decane 
• 35342-70-2 4-methyl-4-phenyl-1,6-heptadiene 

Relevant academic research and scientific papers

Surfactant-Assisted Ozonolysis of Alkenes in Water: Mitigation of Frothing Using Coolade as a Low-Foaming Surfactant

Aqueous-phase ozonolysis in the atmosphere is an important process during cloud and fog formation. Water in the atmosphere acts as both a reaction medium and a reductant during the ozonolysis. Inspired by the atmospheric aqueous-phase ozonolysis, we herein report the ozonolysis of alkenes in water assisted by surfactants. Several types of surfactants, including anionic, cationic, and nonionic surfactants, were investigated. Although most surfactants enhanced the solubility of alkenes in water, they also generated excessive foaming during the ozone bubbling, which led to the loss of products. Mitigation of the frothing was accomplished by using Coolade as a nonionic and low-foaming surfactant. Coolade-assisted ozonolysis of alkenes in water provided the desired carbonyl products in good yields and comparable to those achieved in organic solvents. During the ozonolysis reaction, water molecules trapped within the polyethylene glycol region of Coolade were proposed to intercept the Criegee intermediate to provide a hydroxy hydroperoxide intermediate. Decomposition of the hydroxy hydroperoxide led to formation of the carbonyl product without the need for a reductant typically required for the conventional ozonolysis using organic solvents. This study presents Coolade as an effective surfactant to improve the solubility of alkenes while mitigating frothing during the ozonolysis in water.

Selectivity in Lewis acid-mediated fragmentations of peroxides and ozonides: Application to the synthesis of alkenes, homoallyl ethers, and 1,2-dioxolanes

Fragmentation of dialkyl peroxides and ozonides is strongly influenced by the choice of Lewis acid. TiCl4 promotes C-O ionization (SN1 reaction) of tertiary peroxides while SnCl4 and BF3·OEt2 promote O-O heterolysis (Hock reaction). The cationic intermediates are trapped with allyltrimethylsilane to afford allylated alkanes and homoallyl ethers. In the absence of a nucleophile, ozonides (1,2,4-trioxolanes) invariably undergo O-O heterolysis. However, the combination of allyltrimethylsilane and SnCl4 results in formation of 1,2-dioxolanes via trapping of intermediates derived from SN1 ionization.

SnCl4-mediated reaction of ozonides with allyltrimethylsilane: Formation of 1,2-dioxolanes

SnC14-mediated reaction of ozonides (1,2,4-trioxolanes) with allyltrimethylsilane furnishes trimethylsilylmethyl-1,2-dioxolanes via metalated carbonyl oxides. The carbonyl oxides can arise through initial ionization of either the ether or peroxide oxygens.

OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XVIII. INVESTIGATION OF A NEW OZONOLYTIC SYNTHESIS OF CARBOXYLIC ACIDS

By identification of the 18O isotope label in the oligomeric peroxide obtained by ozonization of a cyclic olefin in the presence of heavy oxygen and also in the product from catalytic isomerization of this peroxide ( the α,ο-dicarboxylic acids or its dimethyl ester ) it was shown that oxygen enters the ozonolysis product when the reaction is carried out in ether solvents.It is suggested that the increased content of active oxygen in the ozonolysis peroxy product is due to oxidation of the ether solvent to form α-hydroperoxide and addition of the latter to the oligomeric zwitterion, solvated by the polar solvents.It was established that the catalytic and thermal isomerization of the oligomeric peroxides and ozonides of cyclic olefins to the α,ο-dicarboxylic acids and ο-formyl carboxylic acids occurs through the oligomeric α-hydroxy peresters and α-hydroxy esters respectively.