Peroxidation of industrially produced diisopropenylbenzenes as alternative pathway to bis(tert-butylperoxyisopropyl)benzenes, cross-linking agent for elastomers and thermoplastics

Peroxidation of industrially produced diisopropenylbenzenes as alternative pathway to bis(tert-butylperoxyisopropyl)benzenes, cross-linking agent for elastomers and thermoplastics Научная публикация

Журнал

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Вых. Данные

Год: 2026, Том: 183, Номер статьи : 156201, Страниц : DOI: 10.1016/j.tetlet.2026.156201

Авторы

Barsegyan Yana A. ¹ , Lipilin Dmitry L. ¹ , Frumkin Alexander E. ¹ , Bityukov Oleg V. ¹ , Filina Maria P. ² , Vil' Vera A. ¹ , Terent'ev Alexander O. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, Russian Federation
2	Department of Chemistry, Tomsk State University, Arkadii Ivanova st. 49, 634050 Tomsk, Russian Federation

The synthesis of highly desired cross-linking agent for elastomers and thermoplastics, bis(tert-butylperoxyisopropyl)benzenes, is currently disadvantaged by the challenge of accessing the appropriate hydroxy or hydroperoxy-functionalized precursors. A class of starting compounds that shows promise as precursors to bis(tert-butylperoxyisopropyl)benzenes is diisopropenylbenzenes, which are industrially produced and commercially available. However, the application of diisopropenylbenzenes as substrates was not expected due to their tendency to undesirable side condensations and oxidations in the presence of acids and oxidants. This research demonstrates an effective method for the synthesis of bis(tert-butylperoxyisopropyl)benzenes from available diisopropenylbenzenes and tert-butylhydroperoxide using hydrochloric acid as a catalyst. The other strong acids did not exhibit the same efficiency as hydrochloric acid, demonstrating that not only protonation but also a significant contribution from the counterion plays an important role in the peroxidation process. This study offers a more sustainable synthetic pathway to bis(tert-butylperoxyisopropyl)benzenes compared to known industrial oxidation procedures. Here, we show that the proposed pathway has improved available sourcing of raw materials, achieved an 80% yield of 1,3-bis(tert-butylperoxyisopropyl)benzene and an 89% yield of 1,4-bis(tert-butylperoxyisopropyl)benzene for the one-step process, and is more time efficient. While further research on industrial scalability and purification must be conducted, and we will upcoming, this pathway offers potential for sustainably synthesizing desired cross-linking agent.

Barsegyan Y.A. , Lipilin D.L. , Frumkin A.E. , Bityukov O.V. , Filina M.P. , Vil' V.A. , Terent'ev A.O.
Peroxidation of industrially produced diisopropenylbenzenes as alternative pathway to bis(tert-butylperoxyisopropyl)benzenes, cross-linking agent for elastomers and thermoplastics
Tetrahedron Letters. 2026. V.183. 156201 . DOI: 10.1016/j.tetlet.2026.156201 Scopus OpenAlex

Поступила в редакцию:	21 мая 2026 г.
Опубликована online:	8 июл. 2026 г.

≡ Scopus:	2-s2.0-105044036084
≡ OpenAlex:	W7167356783