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  • Selective phenol recovery via simultaneous hydrogenation/dealkylation of isopropyl- and isopropenyl-phenols employing an H2 generator combined with tandem micro-reactor GC/MS.

Selective phenol recovery via simultaneous hydrogenation/dealkylation of isopropyl- and isopropenyl-phenols employing an H2 generator combined with tandem micro-reactor GC/MS.

Scientific reports (2018-09-20)
Shogo Kumagai, Masaki Asakawa, Tomohito Kameda, Yuko Saito, Atsushi Watanabe, Chuichi Watanabe, Norio Teramae, Toshiaki Yoshioka
ABSTRACT

The pyrolysis of bisphenol A (BPA), an essential process ingredient used in industry and many everyday life products, helps produce low-industrial-demand chemicals such as isopropenyl- and isopropyl-phenols (IPP and iPrP). In this study, tandem micro-reactor gas chromatography/mass spectrometry combined with an H2 generator (H2-TR-GC/MS) was employed for the first time to investigate the selective recovery of phenol via simultaneous hydrogenation/dealkylation of IPP and iPrP. After investigating the iPrP dealkylation performances of several zeolites, we obtained full iPrP conversion with over 99% phenol selectivity using the Y-zeolite at 350 °C. In contrast, when applied to IPP, the zeolite acid centres caused IPP polymerisation and subsequent IPP-polymer cracking, resulting in many byproducts and reduced phenol selectivity. This challenge was overcome by the addition of 0.3 wt% Ni on the Y-zeolite (0.3Ni/Y), which enabled the hydrogenation of IPP into iPrP and subsequent dealkylation into phenol (full IPP conversion with 92% phenol selectivity). Moreover, the catalyst deactivation and product distribution over repetitive catalytic use were successfully monitored using the H2-TR-GC/MS system. We believe that the findings presented herein could allow the recovery of phenol-rich products from polymeric waste with BPA macro skeleton.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Isopentenyl pyrophosphate triammonium salt solution, 1 mg/mL in methanol (:aqueous 10 mM NH4OH (7:3)), ≥95% (TLC)
Sigma-Aldrich
4-Isopropylphenol, 98%