Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Synthesis of Helional by Hydrodechlorination Reaction in the Presence of Mono and Bi-metallic Catalysts Supported on Alumina

Oreste Piccolo
* ORCID logo ,
Iztok Arčon
ORCID logo ,
Gangadhar Das
,
Giuliana Aquilante
,
Andrea Prai
,
Stefano Paganelli
ORCID logo ,
Manuela Facchin
ORCID logo ,
Valentina Beghetto
ORCID logo
Version 1 : Received: 25 January 2024 / Approved: 26 January 2024 / Online: 26 January 2024 (09:41:39 CET)

A peer-reviewed article of this Preprint also exists.

Piccolo, O.; Arčon, I.; Das, G.; Aquilanti, G.; Prai, A.; Paganelli, S.; Facchin, M.; Beghetto, V. Synthesis of Helional by Hydrodechlorination Reaction in the Presence of Mono- and Bimetallic Catalysts Supported on Alumina. Catalysts 2024, 14, 255. Piccolo, O.; Arčon, I.; Das, G.; Aquilanti, G.; Prai, A.; Paganelli, S.; Facchin, M.; Beghetto, V. Synthesis of Helional by Hydrodechlorination Reaction in the Presence of Mono- and Bimetallic Catalysts Supported on Alumina. Catalysts 2024, 14, 255.

Abstract

Hydrodechlorination reaction of 3-(benzo-1,3-dioxol-5-yl)-3-chloro-2-methylacrylaldehyde in the presence of different low metal content heterogeneous mono- or bi-metallic catalysts was tested for the synthesis of the fragrance Helional® (3-[3,4-methylendioxyphenyl]-2-methyl-propionaldehyde). In particular, mono Pd/Al2O3, Rh/Al2O3 or bi-metallic Pd-Cu/Al2O3, Rh-Cu/Al2O3 catalysts were tested in different reaction conditions from which it emerged that mono-Rh/Al2O3 was the best performing catalyst allowing to achieve 100% substrate conversion and 99% selectivity towards Helional® in 24h at 80°C, p(H2) 1.0 MPa in the presence of a base. To establish correlations between atomic structure and catalytic activity, catalysts were characterized by Cu, Rh and Pd K-edge XANES, EXAFS analysis. These characterizations allowed to verify that the formation of Pd-Cu alloys and the presence of Cu oxide/hydroxide species on the surface of the Al2O3 support, are responsible for the very low catalytic efficiency of bimetallic species tested.

Keywords

Helional®; selective hydrodechlorination; heterogeneous catalysis; XANES analysis; EXAFS analysis

Subject

Chemistry and Materials Science, Applied Chemistry

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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