Epoxide ring-opening reaction promoted by ionic liquid reactivity: interplay of experimental and theoretical studies

Abstract

Ionic liquids (ILs) have been widely introduced recently into the epoxide ring-opening reaction as catalysts or solvent without considering the chemical stability of ILs in propylene oxide (PO).

Quantitative Control Factors of Double Salt Ionic Liquids Catalysis in the Coupling Reaction of Epoxied and Methanol

“…In this reaction, the ring-opening of PO can be motivated by either nucleophile or electrophile. , That means ILs as catalysts is very suitable in this reaction because cation providing nucleophilic HBD and anion providing electrophilic HBA could have a synergetic effect on PO. The previous works demonstrated the higher efficiency and selectivity of PGME with ILs catalysts than that of traditional catalysts such as NaOH …”

“…The previous works demonstrated the higher efficiency and selectivity of PGME with ILs catalysts than that of traditional catalysts such as NaOH. 6 As it can be seen in Table 2, the coupling reaction of PO with methanol can hardly process without catalysts showing the lowest reaction rate (k). When ILs were as catalysts, the reaction dramatically improved with the value of k increasing more than ten times.…”

“…Judicious variation of the cations and anions give ILs designable properties to act as catalysts or solvent in the reaction. It has been reported that hydrogen bonding, charge–charge interaction, acid–base properties, and coordination of ILs plays significant roles in their catalytic performance even new reaction mechanism in IL catalysis. − For example, the coupling reaction of epoxide and substrate could be motivated by IL easily because of the cooperative effect of nucleophilic anion and electrophilic cation, further exploited for the synthesis of added-value products from CO 2 or alcohol, such as propylene carbonate (PC), propylene glycol methyl ether (PGME), and polycarbonates . It is an efficient and high atom economy synthesis route for C–O construction from green, cheap, and bulk stock.…”

Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis

“…As an important strategy widely applied for natural phenols such as chavicol and honokiol to generate diverse derivatives [ 73 , 74 ], allyl-benzene fragments can be epoxidized by peroxy acid, after which a great variety of nucleophilic groups including hydroxyl, alkoxyl, aryloxyl, halogen and amino could be introduced [ 75 , 76 ] (Scheme 6 n–p). Affected by periodic acid or periodate, epoxide can be cleaved and transformed to corresponding aldehyde [ 77 , 78 ] (Scheme 6 q).…”

Synthesis of core–shell Ce-modified mixed metal oxides derived from P123-templated layered double hydroxides

“…Although traditional solid base catalysts such as NaOH and KOH have good catalytic activity in similar alkoxylation reactions, such homogeneous and highly corrosive substances do great harm to industrial equipment and increase the difficulty of product refining. Recent researches of alcohol ether synthesis took ionic liquids 5 and zeolitic imidazolate framework (ZIF-8) 6 as important research objects. These new types of catalysts can achieve a high PO conversion rate with a relatively small amount of use, but they become a stumbling block in the product purification process.…”