1874-62-0

Usage

Uses

3-Ethoxy-1,2-propanediol is a possbile antiknock additive for gasoline and diesel fuel.

InChI:InChI=1/C5H12O3/c1-2-8-4-5(7)3-6/h5-7H,2-4H2,1H3

Upstream product

• 557-31-3 3-ethoxyprop-1-ene 
• 359-48-8 trifluoroacetyl peroxide 
• 96-23-1 1,3-Dichloro-2-propanol 
• 64-17-5 ethanol 
• 556-52-5 oxiranyl-methanol 
• 141-52-6 sodium ethanolate 
• 96-24-2 3-monochloro-1,2-propanediol 
• 80-05-7 BPA 
• 2463-45-8 4-chloromethyl-[1,3]dioxolan-2-one 
• 107-18-6 allyl alcohol 
• 74-96-4 ethyl bromide 
• 56-81-5 glycerol 
• 67-64-1 acetone 
• 71-36-3 butan-1-ol 

Downstream Products

• 71-23-8 propan-1-ol 
• 64-17-5 ethanol 
• 4359-46-0 2-ethyl-4-methyl-1,3-dioxolane 
• 545581-50-8 2-ethyl-4-ethoxymethyl-1,3-dioxolane 

Relevant academic research and scientific papers

Control of Product Selectivity for the Epoxidation of Allyl Alcohol by Variation of the Acidity of the Catalyst TS-1

The acidity of TS-1 controls the product selectivity for the epoxidation of allyl alcohol with H2O2; base treatment of TS-1 enhances the selectivity to glycidol whereas incorporation of Broensted acid sites enhances the selectivity to the products of solvolysis ring opening reactions.

Regioselective Ring-Opening of Glycidol to Monoalkyl Glyceryl Ethers Promoted by an [OSSO]-FeIII Triflate Complex

A FeIII-triflate complex, bearing a bis-thioether-di-phenolate [OSSO]-type ligand, was discovered to promote the ring-opening of glycidol with alcohols under mild reaction conditions (0.05 mol % catalyst and 80 °C). The reaction proceeded with high activity (initial turnover frequency of 1680 h?1 for EtOH) and selectivity (>95 %) toward the formation of twelve monoalkyl glyceryl ethers (MAGEs) in a regioselective fashion (84–96 % yield of the non-symmetric regioisomer). This synthetic approach allows the conversion of a glycerol-derived platform molecule (i.e., glycidol) to high-value-added products by using an Earth-crust abundant metal-based catalyst.

Optimization of the synthesis of glycerol derived monoethers from glycidol by means of heterogeneous acid catalysis

We present an efficient and green methodology for the synthesis of glycerol monoethers, starting from glycidol and different alcohols, by means of heterogeneous acid catalysis. A scope of Br?nsted and Lewis acid catalysts were applied to the benchmark reaction of glycidol and methanol. The selected catalysts were cationic exchangers, such as Nafion NR50, Dowex 50WX2, Amberlyst 15 and K10-Montmorillonite, both in their protonic form and exchanged with Al(III), Zn(II) and Fe(III). Thus, total conversions were reached in short times by using 1 and 5% mol catalyst loading and room temperature, without the need for excess glycidol or the presence of a solvent. Finally, these conditions and the best catalysts were successfully applied to the reaction of glycidol with several alcohols such as butanol or isopropanol.

Synthesis of 3-alkoxypropan-1,2-diols from glycidol: Experimental and theoretical studies for the optimization of the synthesis of glycerol derived solvents

A straightforward synthetic methodology has been derived for the synthesis of glycerol monoethers from glycidol and alcohols. Several homogeneous and heterogeneous basic catalysts have been tested, the best results being obtained with readily available and inexpensive alkaline metal hydroxides. In the best case, good yield of the desired monoether is obtained under smooth reaction conditions, always with total conversion of glycidol. The selectivity of the reactions mainly depends on the alcohol used, due to the concurrence of undesired side reactions. A mechanistic study carried out through computational DFT calculations, in which solvent effects are taken into account, also complemented the experiments, has allowed to identify the main reaction paths taking place under reaction conditions, giving insights into the main causes affecting the reaction selectivity and also into how it could be improved.

Glycerol as a source of designer solvents: Physicochemical properties of low melting mixtures containing glycerol ethers and ammonium salts

In this work we report the preparation of mixtures of several alkyl glyceryl ethers, as hydrogen bond donor compounds, with two ammonium salts, choline chloride and N,N,N-triethyl-2,3-dihydroxypropan-1-aminium chloride. The stability of the mixtures at different molar ratios and temperatures has been evaluated in order to determine the formation of low melting mixtures. Liquid and stable mixtures have been characterized and their physico-chemical properties such as density, viscosity, refractive index, conductivity and surface tension have been measured in the temperature range of 293.15 K to 343.15 K. Comparison of the mixtures prepared herein with the ones containing glycerol and choline chloride evidences the possibility of tuning the physico-chemical properties by changing the substitution pattern in the hydrogen bond donor compound or in the ammonium salt, thus broadening the scope of application of these mixtures.

Synthesis of Monoalkyl Glyceryl Ethers by Ring Opening of Glycidol with Alcohols in the Presence of Lewis Acids

The present work deals with the production of monoalkyl glyceryl ethers (MAGEs) through a new reaction pathway based on the reaction of glycidol and alcohols catalyzed by Lewis acid-based catalysts. Glycidol is quantitatively converted with high selectivity (99 %) into MAGEs under very mild reaction conditions (80 °C and 0.01 mol % catalyst loading) in only 1 h using Al(OTf)3 or Bi(OTf)3 as catalyst. The proposed method enhances the choice of possible green synthetic approaches for the production of value-added products such as MAGEs.

Synthesis of biodiesel without formation of free glycerol

A new approach to the synthesis of biodiesel has been developed on the basis of alcoholysis of a triglyceride in combination with acetalization of glycerol with lower carbonyl compounds or acetals derived therefrom. A model synthesis of biodiesel not involving free glycerol has been accomplished using rapeseed oil and acid catalysts, as well as without a catalyst under generation of ethanol supercritical fluid; in the latter case, monoalkyl glycerol ethers are formed in addition to the expected cyclic ketals.

Ecotoxicity studies of glycerol ethers in Vibrio fischeri: checking the environmental impact of glycerol-derived solvents

The toxicities of a series of glycerol mono-, di-, and trialkyl ethers against Vibrio fischeri bacteria have been determined. A systematic study has been carried out and the possible structure-toxicity relationships have been discussed using different QSAR models. Inhibition of bioluminescence after 30 minutes of exposure shows relatively low toxicity of many of the glycerol derived chemicals studied. Results indicate that, as a general rule, the ecotoxicity increases with the length and number of substituents. However, if the size of the molecule increases, an extra substituent at position 2 makes the toxicity lower than that of the corresponding analogues.

Thermodynamic characteristics of the sorption of glycerol ethers on stationary phase OV-101

Retention characteristics, temperature dependences of the retention characteristics, and thermodynamic characteristics of sorption on the nonpolar OV-101 phase are determined for 33 glycerol mono-, di-, and triethers with linear and branched monobasic alc

FUEL COMPOSITIONS COMPRISING HYDROPHOBIC DERIVATIVES OF GLYCERINE

The object of the present invention relates to a composition that can be used as fuel comprising: at least one hydrocarbon mixture at least one hydrophobic ketal or acetal of glycerine. Said composition can be advantageously used as fuel for diesel or gasoline engines.