Kinetics and Mechanism of the Ozone Reaction with Alcohols, Ketones, Ethers and Hydroxybenzenes

Abstract

Abstract. The review, based on 92 references, is focused on degradation of organics by ozonation and it comprises various classes of oxygen-containing organic compounds -alcohols, ketones, ethers and hydroxybenzenes. The mechanisms of a multitude of ozone reactions with these compounds in organic solvents are discussed in details, presenting the respective reaction schemes. The corresponding kinetic parameters are given and some thermodynamic parameters are also listed. The dependences of the kinetics and the mechanism of the ozonation reactions on the structure of the compounds, on the medium and on the reaction conditions are revealed. Various possible applications of ozonolysis are specified and discussed. All these reactions have practical importance for the protection of the environment.

Facile Ozonation of Light Alkanes to Oxygenates with High Atom Economy in Tunable Condensed Phase at Ambient Temperature

“…In addition, an apparent inhibition by dioxygen is revealed [as seen in the denominator of the k i P O 3 /(1 + K o P O 2 ) term], especially at low P O 3 . The initiation steps of saturated hydrocarbons with ozone have been proposed to involve radical formation as follows. , normalR − normalH + normalO 3 → normalR • + HOO normalO • → normalR OOOH → normalR normalO • + HO normalO • normalR normalO • + normalR − normalH → normalR OH + normalR • normalR • + normalO 3 → normalR OO R • The R • radical may be intercepted by dioxygen to produce a less active peroxyl intermediate, slowing down the overall activation rate. , normalR • + normalO 2 → normalR normalO normalO • …”

“…Thus, this inhibition effect could be evidence that the assumed intermediate shared by acetone and tert -butyl alcohol formation is likely to be tert -butyl hydrotrioxide or its derivative. As suggested by the observations during the ozonation of butanone and isobutane, dioxygen potentially inhibits other reactions involving H-atom abstraction during the initiation steps, such as the ozonation of 2-butanol , and n -butane.…”

“…Ozone attacks most organic solvents more readily than it activates alkanes, which adversely affects the efficient utilization of ozone. Solvents such as chlorocarbons − and fluorocarbons − display enhanced resistance to ozone. However, these solvents pose environmental concerns. , While acetic acid can serve as a more environmentally benign solvent that is resistant to ozone oxidation, this solvent acts as a radical scavenger and thus does not act as an innocent solvent .…”

Enhancing the Wettability of Polyetheretherketone (Peek) Membrane with Ozone for Improving Fuel Cell Performance

“…Since the reaction of ozone with ethers in organic solutions indicate the attachment of ozone to α-hydrogen near the ether group [37], Figure 7 shows ozonation of the unsaturated C-C sp 2 bond closest to the ether group in PEEK to form a primary ozonide [38] similar to the reaction of ozone with the fuel cell membrane polybenzimdazole (PBI) [18]. Figure 7 displays the possible decomposition steps marked "a" and "b" in addition to breakage of the "c" bond.…”

Gas-liquid-liquid reactions: Contacting mechanisms and effective process technologies

“…It produced 1, 2, 3 trioxolane/primary ozonide, which rapidly decomposed to form carbonyl oxide /zwitterions and carbonyl compounds (aldehyde/ketone). The greatest challenge encountered to achieve high yields of product is mainly related to the solubility of ozone in the liquid solution [25], [26]. Riadi et al [14] also faced similar difficulties to achieve high yields of the ozonolysis reaction.…”