Benign synthesis of terpene-based 1,4-p-menthane diamine

Terpenes represent a promising renewable feedstock for the substitution of fossil resources in the synthesis of renewable platform chemicals, like diamines. This work describes the synthesis and full characterization of 1,4- p -menthane diamine ( 1,4-PMD ) obtained from α -terpinene ( 1 ). A two-ste...

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Bibliographic Details
Published in:Scientific reports 2024-04, Vol.14 (1), p.8055-8055, Article 8055
Main Authors: Wenzel, Jonas O., Santos Correa, Luis, Schmidt, Sarah, Meier, Michael A. R.
Format: Article
Language:English
Subjects:
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639/638/403
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Amination
Ammonia
Chemistry
Humanities and Social Sciences
Hydrogenation
Investigations
multidisciplinary
Nitrogen
p-Menthane
Raw materials
Reagents
Science
Science (multidisciplinary)
Terpinene
Toxicity
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Summary:Terpenes represent a promising renewable feedstock for the substitution of fossil resources in the synthesis of renewable platform chemicals, like diamines. This work describes the synthesis and full characterization of 1,4- p -menthane diamine ( 1,4-PMD ) obtained from α -terpinene ( 1 ). A two-step procedure using dibenzyl azodicarboxylate (DBAD) and H 2 as rather benign reagents was employed under comparatively mild conditions. Both C–N bonds were formed simultaneously during a visible-light mediated Diels–Alder reaction, which was investigated in batch or flow, avoiding regioselectivity issues during the amination steps that are otherwise typical for terpene chemistry. Heterogeneously catalyzed quadruple hydrogenation of the cycloadduct ( 2a ) yielded 1,4‑PMD ( 3 ). While the intermediate cycloadduct was shown to be distillable, the target diamine can be sublimed, offering sustainable purification methods.
ISSN:2045-2322
2045-2322
DOI:10.1038/s41598-024-58615-5