Glycerol acetals and ketals as possible diesel additives. A review of their synthesis protocols

Trifoi, Ancuța; Agachi, Paul Şerban; Pap, Timea

doi:10.1016/j.rser.2016.05.013

Cited by 117 publications

(76 citation statements)

References 53 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In the case of the acetalization of aldehydes and ketones with glycerol, the cyclic acetals,1 ,3-dioxolanes and 1,3-dioxanes (see Scheme 2), are obtained in differentr atios depending on experimental conditions and catalyst. [16] On the other hand, when HMF is involved in etherification or acetalization reactions, the selectivity to the target compoundc an be strongly affected owing to its high reactivity. The bifunctionality of HMF possessing an alcohol and an aldehyde functions can give, in the presenceo fa na lcohol and an acid catalyst, etherified and at the same time acetalized derivatives.…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Synthesis of Biomass‐Derived Surfactants by Reacting Hydroxymethylfurfural, Glycerol, and Fatty Alcohols on Solid Acid Catalysts

et al. 2018

View full text Add to dashboard Cite

A new type of biomass-derived non-ionic surfactants has been obtained by reacting hydroxymethylfurfural (HMF), glycerol, and fatty alcohols. For instance, 5-(octyloxymethyl)furfural glyceryl acetal can be obtained in a one-pot process by etherification of HMF with fatty alcohols followed by acetalization with glycerol. For a successful solid catalyst, acidity and polarity have to be optimized to improve conversion, selectivity, and catalyst deactivation owing to the different adsorption characteristics of the reactant molecules. Accordingly, Beta zeolite with a high Si/Al ratio and practically free of connectivity defects showed good results when dealing with these biomass derivatives, which include a highly polar reactant such as glycerol. The scope of the reaction is good and a variety of new stable surfactant molecules can be obtained that present hydrophilic-lipophilic balance (HLB ) values in the range 4.9 to 6.6, which are of interest for water in oil emulsions.

show abstract

Section: Introductionmentioning

confidence: 99%

One‐Pot Synthesis of Biomass‐Derived Surfactants by Reacting Hydroxymethylfurfural, Glycerol, and Fatty Alcohols on Solid Acid Catalysts

et al. 2018

View full text Add to dashboard Cite

show abstract

“…H + was soluble in the xylitol aqueous before the reaction. According to the mechanism of the acetalization reaction, the aldehyde is first protonated with the H + and then interacts with alcohol. So, the H + needed to migrate from xylitol aqueous to n‐octanal.…”

Section: Resultsmentioning

confidence: 99%

The Hydrolysis Equilibrium Effect of Water with Cu(II) Catalysts Used for the Selective Synthesis of Xylitol Monoacetals as Bio‐Based Surfactants

Tang

Dong

2019

ChemistrySelect

View full text Add to dashboard Cite

Xylitol obtained from the biomass was converted into selective products via acetalization with long‐chain aldehydes in the presence of water. The results demonstrate that CuSO4 may be a promising catalyst for the synthesis of monoacetals from n‐octanal. Upon adding the corresponding sodium salt to inhibit the hydrolysis reaction, CuSO4 was less efficient at promoting the reaction when compared to other soluble copper salts (CuCl2, Cu(NO3)2 and Cu(OTf)2) because of its low Lewis acid activity in water. According to the results obtained under different pH conditions, the CuSO4 catalyst was able to selectively prepare the monoacetal because the initial reaction rate was controlled using gradual hydrolysis. Two other monoacetals obtained from n‐hexanal and n‐decanal were also synthesized. In addition, the surfactant properties of all the as‐prepared monoacetals were evaluated.

show abstract

“…Acetals and ketals of glycerol are obtained via direct acid‐catalyzed condensation of glycerol with carbonyl compounds, via transacetalization of glycerol by corresponding dimethylacetals, or through addition of carbonyl compounds to glycidol in the presence of Lewis acids (Scheme ). For the direct acetalization starting from glycerol and carbonyl compounds both homogeneous (sulfuric acid,, p‐TSA, sulfonated polyvinyl alcohol, Fe(III) and Sn(II)salts) and heterogeneous acid catalysts (the most promising for the industrial application here are zeolites, and sulfonic ion‐exchange resins,,,).…”

Section: Introductionmentioning

confidence: 99%

“…Acetals and ketals of glycerol are obtained via direct acidcatalyzed condensation of glycerol with carbonyl compounds, [18] via transacetalization of glycerol by corresponding dimethylacetals [19,20] or through addition of carbonyl compounds to glycidol in the presence of Lewis acids [21] (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Transacetalization of Solketal: A Greener Route to Bioglycerol‐Based Speciality Chemicals

Samoilov

Maximov

2018

ChemistrySelect

View full text Add to dashboard Cite

In the present study the potential of solketal transacetalization reaction has been demonstrated as an effective method of synthesis of acetals of glycerol and lipophilic carbonyl compounds (2‐ethylhexanal, n‐decanal, cyclopentanone, cyclohexanone). In solketal transacetalization with 2‐ethylhexanal reaction rate was significantly higher than of direct acetalization of glycerol both with and without a solvent because on the contrary to glycerol solketal is freely miscible with lipophilic compounds. Unlike the direct acetalization, reaction rate increased along with the temperature with no losses in equilibrium conversion. Furthermore, by stripping of by‐product acetone from the reaction zone we have succeeded in increasing the product yield in one‐pot synthesis to 97–98%, so that no further purification is needed. Finally, transacetalization was shown to be catalyzed with solid acids much more efficiently than the direct reaction (the cheap and eco‐friendly montmorillonite K‐10 catalyst was found to be the most active). Based on the regulations revealed, a green atom‐efficient synthetic protocol to obtain higher glycerol acetals and ketals has been proposed.

show abstract

Glycerol acetals and ketals as possible diesel additives. A review of their synthesis protocols

Cited by 117 publications

References 53 publications

One‐Pot Synthesis of Biomass‐Derived Surfactants by Reacting Hydroxymethylfurfural, Glycerol, and Fatty Alcohols on Solid Acid Catalysts

One‐Pot Synthesis of Biomass‐Derived Surfactants by Reacting Hydroxymethylfurfural, Glycerol, and Fatty Alcohols on Solid Acid Catalysts

The Hydrolysis Equilibrium Effect of Water with Cu(II) Catalysts Used for the Selective Synthesis of Xylitol Monoacetals as Bio‐Based Surfactants

Transacetalization of Solketal: A Greener Route to Bioglycerol‐Based Speciality Chemicals

Contact Info

Product

Resources

About