15821-83-7Relevant articles and documents
Synthesis of propylene glycol ethers from propylene oxide catalyzed by environmentally friendly ionic liquids
Zhao, Cong,Chen, Shengxin,Zhang, Ruirui,Li, Zihang,Liu, Ruixia,Ren, Baozeng,Zhang, Suojiang
, p. 879 - 888 (2017/05/24)
A series of acetate ionic liquids were synthesized using a typical two-step method. The ionic liquids were used as environmentally benign catalysts in the production of propylene glycol ethers from propylene oxide and alcohols under mild conditions. The basic strengths of the ionic liquids were evaluated by determination of their Hammett functions, obtained using ultraviolet-visible spectroscopy, and the relationship between their catalytic activities and basicities was established. The catalytic efficiencies of the ionic liquids were higher than that of the traditional basic catalyst NaOH. This can be attributed to the involvement of a novel reaction mechanism when these ionic liquids are used. A possible electrophilic-nucleophilic dual activation mechanism was proposed and confirmed using electrospray ionization quadrupole time-of-flight mass spectrometry. In addition, the effects of significant reaction parameters such as concentration of catalyst, molar ratio of alcohol to propylene oxide, reaction temperature, and steric hindrance of the alcohol were investigated in detail.
Catalytic etherification of glycerol with short chain alkyl alcohols in the presence of Lewis acids
Liu, Fei,De Oliveira Vigier, Karine,Pera-Titus, Marc,Pouilloux, Yannick,Clacens, Jean-Marc,Decampo, Floryan,Jerome, Francois
, p. 901 - 909 (2013/07/26)
Here we report the homogeneously-catalyzed etherification of glycerol with short chain alkyl alcohols. Among the large variety of Bronsted and Lewis acids tested, we show here that metal triflates are not only the most active but are also capable of catalyzing this reaction with an unprecedented selectivity. In particular, in the presence of Bi(OTf)3, the targeted monoalkylglyceryl ethers were obtained with up to 70% yield. Although tested Bronsted acids were also capable of catalyzing the etherification of glycerol with alkyl alcohols, they were found however less active and less selective than Bi(OTf)3. By means of counter experiments, we highlighted that the high activity and selectivity of Bi(OTf)3 may rely on a synergistic effect between Bi(OTf)3 and triflic acid, a Bronsted acid that can be released by in situ glycerolysis of Bi(OTf)3. The scope of this methodology was also extended to other polyols and, in all cases, the monoalkylpolyol ethers were conveniently obtained with fair to good yields.
Tunable synthesis of propylene glycol ether from methanol and propylene oxide under ambient pressure
Bai, Yu,Cai, Qinghai,Wang, Xiaoguang,Lu, Bin
experimental part, p. 386 - 390 (2011/08/04)
A series of basic and acidic ionic liquids, 1-butyl-3-methylimidazolium hydroxide (BMIMOH), 1-acetyl-3-methylimidazolium chloride (AcMIMCl) and AcMIMCl-FeCl3, or analogues of AcMIMCl, namely 1-potassium acetate-3-methylimidazolium chloride (KAcMIMCl), 1-potassium (sodium, ammonium) acetate-3-methylimidazolium hydroxides (KAcMIMOH, NaAcMIMOH and NH 4AcMIMOH), were prepared and used as catalysts for catalytic synthesis of propylene glycol ether via reaction of propylene oxide (PO) with methanol under mild reaction conditions. KAcMIMOH exhibited outstanding catalytic performance with 94.2% of conversion of PO and 99.1% of selectivity to 1-methoxy-2-propanol (MP-2) at 60°C and ambient pressure for 4 h. However, AcMIMCl-FeCl3 showed a good catalysis performance with high selectivity to 2-methoxy-1-propanol (MP-1). The tunable synthesis of MP-2 or MP-1 catalyzed by basic compound KAcMIMOH or acidic ionic liquid AcMIMCl-FeCl3 was realized.
