A Highly Regioselective and Solvent-Free Sn(II)-Catalyzed Glycerol Ketals Synthesis at Room Temperature

Silva, Márcio José da; Guimaraes, Matheus de Oliveira; Júlio, Armanda Aparecida

doi:10.1007/s10562-015-1477-8

Cited by 30 publications

(24 citation statements)

References 24 publications

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“…According to literature data, the benzaldehyde ketal consisted of a mixture of the five- and six-membered products, 39 as revealed by the NMR spectrum in deuterated methanol. As expected, 69 less satisfying were the outcomes of the catalysis with cyclopentanone (entry 4).…”

Section: Resultssupporting

confidence: 65%

Iron(III) Complexes for Highly Efficient and Sustainable Ketalization of Glycerol: A Combined Experimental and Theoretical Study

et al. 2019

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The growing production of biodiesel as a promising alternative and renewable fuel led as the main problem the dramatic increase of its by-product: glycerol. Different strategies for glycerol derivatization have been reported so far, some more efficient or sustainable than others. Herein, we report a very promising and eco-friendly transformation of glycerol in nontoxic solvents and chemicals (i.e., solketal, ketals), proposing three new families of Fe(III) compounds capable of catalysing glycerol acetalization with unpublished turn over frequencies (TOFs), and adhering most of the principles of green chemistry. The comparison between the activity of complexes of formula [FeCl 3 ( 1-R )] ( 1-R = substituted pyridinimine), [FeCl( 2-R , R′ )] ( 2-R , R′ = substituted O , O ′-deprotonated salens) and their corresponding simple salts reveals that the former are extremely convenient because they are able to promote solketal formation with excellent TOFs, up to 10 5 h –1 . Satisfactory performances were shown with respect to the entire range of substrates, with results being competitive to those reported in the literature so far. Moreover, the experimental activity was supported by an accurate and complete ab initio study, which disclosed the fundamental role of iron(III) as Lewis acid in promoting the catalytic activity. The unprecedented high activity and the low loading of the catalyst, combined with the great availability and the good eco-toxicological profile of iron, foster future applications of this catalytic process for the sustainable transformation of an abundant by-product in a variety of chemicals.

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Section: Resultssupporting

confidence: 65%

Iron(III) Complexes for Highly Efficient and Sustainable Ketalization of Glycerol: A Combined Experimental and Theoretical Study

et al. 2019

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“…In our preliminary study, we carried out solvent‐free esterification of dimer acid and 1‐octanol (mole ratio 1:2) catalyzed by tin(II) oxalate (1 wt%) by heating at 200 °C for 7 h. We employed tin(II) salt as the Lewis acid catalyst as it is a stable solid, highly tolerant to water, easily handled, less corrosive, inexpensive, and accessible commercial Lewis acid catalysts, and have shown high activity on esterification reactions . Due to these properties, the use of organotin as a potential catalyst to produce esters for biodiesel, lubricant, and alkyd resin has become a new interest. In addition, this tin‐based catalyst is found to be efficient in solvent‐free reaction conditions …”

Section: Resultsmentioning

confidence: 99%

Excellent Properties of Dimer Fatty Acid Esters as Biolubricant Produced by Catalyst‐ and Solvent‐Free Esterification

Armylisas

Fauzi

Mohd

et al. 2019

Euro J Lipid Sci & Tech

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Currently most technologies available to produce esters require acid or base catalysts for esterification or transesterification reactions. Production of dimerate esters (DE) exhibiting potential as a biolubricant for low temperature applications using catalyst‐ and solvent‐free approaches is presented in this article. Hydrogenated C36 dimer acid and alcohol are reacted under the following conditions: dimer acid/alcohol (1:4.5 molar ratio), 150–200 °C, 24 h, 3Å molecular sieve (15% w/w). The performances of four DE species—dibutyl, dihexyl, di‐(2‐ethylhexyl), and dioctyl dimerate—as lubricant base stocks are evaluated by kinematic viscosity, viscosity index, cloud and pour point (cold flow properties) as well as oxidative stability, and compared with commercial synthetic lubricant base stock and DE, Radialube 7121. High viscosity indexes ranging between 129 and 138 are observed for the synthesized DEs, which are comparable with two commercial base stock, polyalpha olefin (PAO), and polyolester (POE). Significantly low pour point, less than −42 °C, is observed for di‐(2‐ethylhexyl) dimerate attributed to the branching of the side chain. The DEs are categorized as ISO VG 68 based on their viscosity according to ISO 3448 classification and show potential as biolubricant with high viscosity index and excellent cold flow properties. Practical Applications: DFAE obtained have high potential to be used as lubricant base stock for equipment and machinery operating at extremely low temperature.

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“…Compared with acetonitrile, and N,N dimethyl formamide, dimethylsulfoxide solvent exhibited better results owing to its capacity toward the catalyst adsorbents, inertness, and miscibility with the reaction medium. da Silva et al ( 2015a ) used an available, environmentally friendly, efficient and simple tin-based catalyst for the ketalization of glycerol with different ketones at 25°C. The ketones conversions were 40 and 98% for 4-methyl 2 pentanone and cyclohexanone, respectively.…”

Section: Impacts Of Various Reaction Parameters On Catalytic Performamentioning

confidence: 99%

A Review on the Catalytic Acetalization of Bio-renewable Glycerol to Fuel Additives

et al. 2018

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The last 20 years have seen an unprecedented breakthrough in the biodiesel industry worldwide leads to abundance of glycerol. Therefore, the economic utilization of glycerol to various value-added chemicals is vital for the sustainability of the biodiesel industry. One of the promising processes is acetalization of glycerol to acetals and ketals for applications as fuel additives. These products could be obtained by acid-catalyzed reaction of glycerol with aldehydes and ketones. Application of different supported heterogeneous catalysts such as zeolites, heteropoly acids, metal-based and acid-exchange resins have been evaluated comprehensively in this field. In this review, the glycerol acetalization has been reported, focusing on innovative and potential technologies for sustainable production of solketal. In addition, the impacts of various parameters such as application of different reactants, reaction temperature, water removal, utilization of crude-glycerol on catalytic activity in both batch and continuous processes are discussed. The outcomes of this research will therefore significantly improve the technology required in tomorrow's bio-refineries. This review provides spectacular opportunities for us to use such renewables and will consequently benefit the industry, environment and economy.

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A Highly Regioselective and Solvent-Free Sn(II)-Catalyzed Glycerol Ketals Synthesis at Room Temperature

Cited by 30 publications

References 24 publications

Iron(III) Complexes for Highly Efficient and Sustainable Ketalization of Glycerol: A Combined Experimental and Theoretical Study

Iron(III) Complexes for Highly Efficient and Sustainable Ketalization of Glycerol: A Combined Experimental and Theoretical Study

Excellent Properties of Dimer Fatty Acid Esters as Biolubricant Produced by Catalyst‐ and Solvent‐Free Esterification

A Review on the Catalytic Acetalization of Bio-renewable Glycerol to Fuel Additives

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