4 years ago

Zeolite-Catalyzed Formaldehyde–Propylene Prins Condensation

Zeolite-Catalyzed Formaldehyde–Propylene Prins Condensation
Efterpi S. Vasiliadou, Nicholas S. Gould, Raul F. Lobo
Prins condensation of formaldehyde with propylene to form 3-buten-1-ol is investigated using microporous solid acid catalysts. Zn/H-beta shows high conversion but leads to a broad product distribution composed primarily of pyrans. Mechanistic studies revealed that 3-buten-1-ol reacts via Prins cyclization or dehydrate to 1,3-butadiene that further reacts with formaldehyde via a hetero-Diels–Alder reaction. These secondary reactions are suppressed over ZSM-5 catalysts: 3-buten-1-ol is the predominant product over H-ZSM-5 zeolite under all conditions investigated. 3-Buten-1-ol selectivity of up to 75 % is achieved. In a second step 3-buten-1-ol dehydrates at temperatures as low as 423 K, forming 1,3-butadiene. Although Brønsted acid sites are the primary catalytic sites, ion exchange of ZnII increases the overall rate and 3-buten-1-ol selectivity. H-ZSM-5 showed significant differences in reactivity and selectivity as a function of the Si/Al ratio; optimal catalytic properties were observed within Si/Al=40–140. Substituting homogenous acids: Prins condensation between formaldehyde and propylene is traditionally catalyzed by homogeneous acids. The first experimental evidence is reported of the reaction over microporous solid acid catalysts. It was determined that H-ZSM-5 (MFI) is the optimal catalyst favoring selective formation of 3-buten-1-ol. In a second step, 3-buten-1-ol easily dehydrates to 1,3-butadiene.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/cctc.201701315

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