From Symmetric Glycerol Derivatives to Dissymmetric Chlorohydrins

Solarte, Carmen; Escribà, Marc; Eras, Jordi; Villorbina, Gemma; Canela, Ramón; Balcells, Mercè

doi:10.3390/molecules16032065

Cited by 7 publications

(9 citation statements)

References 29 publications

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“…Products 1a – 1i were synthesized using the method previously described by our group [24], using glycerol and the corresponding carboxylic acid as starting materials. Subsequently, the chloride was replaced by the azide group using a previously reported technique [25].…”

Section: Resultsmentioning

confidence: 99%

“…Starting materials and solvents were purchased from Sigma-Aldrich España (Madrid, Spain), Honeywell Fluka (Madrid, Spain), Supelco (Madrid, Spain) and Across(Madrid, Spain) and were used without further purification. The diazides ( 1a – 1i ) were synthesized from glycerol and the corresponding carboxylic acid following the procedure described before [24] (see Supplementary Materials). The crude product of the reaction was not purified due to its instability and was used for the hydrogenation reaction described below.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis and Thermophysical Characterization of Fatty Amides for Thermal Energy Storage

et al. 2019

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Nine monoamides were synthesized from carboxylic acids (C8–C18) and crude glycerol. The final monoamides were the result of a rearrangement of the acyl chain during the final hydrogenation process. The purity of the final compounds was determined by spectroscopic and mass spectrometry (MS) techniques. The thermophysical properties of solid monoamides were investigated to determine their capability to act as phase change materials (PCM) in thermal energy storage. Thermophysical properties were determined with a differential scanning calorimeter (DSC). The melting temperatures of the analyzed material ranged from 62.2 °C to 116.4 °C. The analyzed enthalpy of these monoamides ranged from 25.8 kJ/kg to 149.7 kJ/kg. Enthalpy values are analyzed considering the carbon chain and the formation of hydrogen bonds.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Synthesis and Thermophysical Characterization of Fatty Amides for Thermal Energy Storage

et al. 2019

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“…The 3-chloro-2-hydroxypropyl esters 1 were synthesized following a procedure reported in the literature. 26 The ruthenium complex (Bäckvall's catalyst) (h 5 -Ph 5 Cp)Ru(CO) 2 Cl was prepared following a procedure described elsewhere. 15 1 H and 13 C NMR spectra were recorded using a Varian AS400 MERCURY Plus at 400 and 100 MHz, respectively.…”

Section: Methodsmentioning

confidence: 99%

“…Procedure A (compounds 1a, 2a Characterization data of products 3-Chloro-2-hydroxyprop-1-yl pivaloate (1a). 26 Colourless liquid. 1 3-Chloro-2-hydroxyprop-1-yl-2-methyl-2-phenyl propanoate (1b).…”

Section: Chiral Analysismentioning

confidence: 99%

Preparation of chiral glycerol derivatives using chemoenzymatic approaches

et al. 2014

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Following our preparation of dissymmetric chlorohydrin esters from glycerol, we have used several lipases and whole cells to examine the kinetic resolution (KR) and dynamic kinetic resolution (DKR) of 3-chloro-2hydroxypropyl esters. Regarding the KR, PS-IM, MmL and CALB lipases and whole cells of Aspergillus flavus showed the best selectivity and activity, depending on the compound studied. PS-IM allowed the isolation of (R)-3-chloro-2-hydroxypropyl pivaloate in 34% yield and with >99% enantiomeric excess (ee). DKR was carried out combining the biocatalysts that performed best for KR and suitable reaction conditions for racemization. Whole cells of A. flavus allowed the preparation of enantioenriched (S)-3-chloro-2acetoxypropyl-2-methyl-2-phenyl propanoate in 43% yield and with 79% ee. Lipozyme from Mucor miehei used in a reaction subsequent to DKR allowed the purification of the corresponding enantioenriched (S)-3-chloro-2-acetoxypropyl pivaloate.

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“…To prepare the corresponding diazide derivatives, 1,3-Dichloroprop-2-yl esters were used ( Figure 8) [117,118]. The substitution process was carried out by using a conventional methodology to prepare azides [119].…”

Section: Synthesis Of Diazidesmentioning

confidence: 99%

Preparation and Uses of Chlorinated Glycerol Derivatives

et al. 2020

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Crude glycerol (C3H8O3) is a major by-product of biodiesel production from vegetable oils and animal fats. The increased biodiesel production in the last two decades has forced glycerol production up and prices down. However, crude glycerol from biodiesel production is not of adequate purity for industrial uses, including food, cosmetics and pharmaceuticals. The purification process of crude glycerol to reach the quality standards required by industry is expensive and dificult. Novel uses for crude glycerol can reduce the price of biodiesel and make it an economical alternative to diesel. Moreover, novel uses may improve environmental impact, since crude glycerol disposal is expensive and dificult. Glycerol is a versatile molecule with many potential applications in fermentation processes and synthetic chemistry. It serves as a glucose substitute in microbial growth media and as a precursor in the synthesis of a number of commercial intermediates or fine chemicals. Chlorinated derivatives of glycerol are an important class of such chemicals. The main focus of this review is the conversion of glycerol to chlorinated derivatives, such as epichlorohydrin and chlorohydrins, and their further use in the synthesis of additional downstream products. Downstream products include non-cyclic compounds with allyl, nitrile, azide and other functional groups, as well as oxazolidinones and triazoles, which are cyclic compounds derived from ephichlorohydrin and chlorohydrins. The polymers and ionic liquids, which use glycerol as an initial building block, are highlighted, as well.

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From Symmetric Glycerol Derivatives to Dissymmetric Chlorohydrins

Cited by 7 publications

References 29 publications

Synthesis and Thermophysical Characterization of Fatty Amides for Thermal Energy Storage

Synthesis and Thermophysical Characterization of Fatty Amides for Thermal Energy Storage

Preparation of chiral glycerol derivatives using chemoenzymatic approaches

Preparation and Uses of Chlorinated Glycerol Derivatives

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