3174-74-1Relevant articles and documents
Tetrahydro-4 H-pyran-4-one: From the Laboratory Scale to Pilot Plant Manufacture
Zahim, Sara,Delacroix, Kenny,Carlier, Agathe,Berranger, Thierry,Bergraser, Julie,Echeverria, Pierre-Georges,Petit, Laurent
, p. 199 - 206 (2022/01/12)
This study describes our recent efforts to find an efficient and scalable route to tetrahydro-4H-pyran-4-one using the commercially available starting materials. The route scouting work and the full development of an efficient access to the target are described. This work culminated in the preparation of above 20 kg of the title compound in our pilot plant facility.
Zeolite-Catalyzed Formaldehyde–Propylene Prins Condensation
Vasiliadou, Efterpi S.,Gould, Nicholas S.,Lobo, Raul F.
, p. 4417 - 4425 (2017/11/20)
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 Br?nsted 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.