Selective ozone activation of phenanthrene in liquid CO2

Honghong Shi; Michael Lundin; Andrew Danby; Eden P Go; Abhimanyu Patil; Huaxing Zhou; Timothy A Jackson; Bala Subramaniam

doi:10.1039/d1ra06642k

Selective ozone activation of phenanthrene in liquid CO₂

RSC Adv. 2021 Dec 23;12(1):626-630. doi: 10.1039/d1ra06642k. eCollection 2021 Dec 20.

Authors

Honghong Shi¹, Michael Lundin¹, Andrew Danby¹, Eden P Go², Abhimanyu Patil³, Huaxing Zhou³, Timothy A Jackson^{1

2}, Bala Subramaniam^{1

4}

Affiliations

¹ Center for Environmentally Beneficial Catalysis, University of Kansas Lawrence KS 66047 USA bsubramaniam@ku.edu.
² Department of Chemistry, University of Kansas Lawrence KS 66045 USA.
³ ExxonMobil Research and Engineering Company 1545 Rt 22 East Annandale New Jersey 08801 USA.
⁴ Department of Chemical and Petroleum Engineering, University of Kansas Lawrence KS 66045 USA.

Abstract

We demonstrate liquid CO₂ (8 °C, 4.4 MPa) as a benign medium to perform safe ozonolysis of phenanthrene at near-ambient temperatures. The ozonolysis products consist of several monomeric oxidation products such as diphenaldehyde, diphenic acid and phenanthrenequinone as well as polymeric structures up to 1130 Da. The observed chemical shifts (¹H-6.03 ppm, ¹³C-104.38 ppm) in 2D-NMR spectra of the products confirm the formation of secondary ozonide. Based on the range of observed products, a Criegee-type mechanism is proposed. The ability to deconstruct phenanthrene and produce oxygenated precursors via this technique is particularly of interest in creating new materials from aromatic moieties.