98451-40-2

Upstream product

• 2372-45-4 sodium butanolate 
• 96-24-2 3-monochloro-1,2-propanediol 
• 63991-93-5 3-but-1-en-t-yloxy-propane-1,2-diol 
• 71-36-3 butan-1-ol 
• 2426-08-6 glycidyl n-butyl ether 
• 109-65-9 1-bromo-butane 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 123-72-8 butyraldehyde 
• 56-81-5 glycerol 
• 124-38-9 carbon dioxide 
• 62-53-3 aniline 
• 556-52-5 oxiranyl-methanol 
• 4379-23-1 4-Hydroxymethyl-2-n-propyl-1,3-dioxolan 
• 4740-91-4 5-Hydroxy-2-n-propyl-1,3-dioxan 

Downstream Products

• 2426-08-6 glycidyl n-butyl ether 
• 106881-91-8 1-Butoxy-3-trityloxy-propan-2-ol 
• 84223-13-2 1-(butoxy)-2-propanone 
• 146668-45-3 1-O-butyl-2-O-hexadecanoyl-3-O-p-toluenesulfonylglycerol 
• 146727-96-0 (R)-1-O-butyl-3-O-tosylglycerol 
• 111221-91-1 1-O-butyl-3-O-tosylglycerol 
• 106881-94-1 C₃₃H₃₆O₃ 
• 106882-01-3 C₁₉H₃₄NO₆P 
• 106881-99-6 Phosphoric acid 2-benzyloxy-3-butoxy-propyl ester 2-bromo-ethyl ester 
• 106881-96-3 2-Benzyloxy-3-butoxy-propan-1-ol 

Relevant academic research and scientific papers

An Amphiphilic (salen)Co Complex – Utilizing Hydrophobic Interactions to Enhance the Efficiency of a Cooperative Catalyst

An amphiphilic (salen)Co(III) complex is presented that accelerates the hydrolytic kinetic resolution (HKR) of epoxides almost 10 times faster than catalysts from commercially available sources. This was achieved by introducing hydrophobic chains that increase the rate of reaction in one of two ways – by enhancing cooperativity under homogeneous conditions, and increasing the interfacial area under biphasic reaction conditions. While numerous strategies have been employed to increase the efficiency of cooperative catalysts, the utilization of hydrophobic interactions is scarce. With the recent upsurge in green chemistry methods that conduct reactions ‘on water’ and at the oil-water interface, the introduction of hydrophobic interactions has potential to become a general strategy for enhancing the catalytic efficiency of cooperative catalytic systems. (Figure presented.).

Bifunctional organocatalysts for the conversion of CO2, epoxides and aryl amines to 3-aryl-2-oxazolidinones

A route to synthesize 3-aryl-2-oxazolidinones is developed, which is achieved through a three component reaction between CO2, aryl amines, and epoxides with a binary organocatalytic system composed of organocatalysts and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). The method allows wide scopes of epoxide and aryl amine substrates with various functional groups under mild reaction conditions. The control experiments indicate that a cyclic carbonate is formed via cycloaddition of epoxides with CO2, which further reacts with the β-amino alcohol originating from epoxides and aryl amines, resulting in the formation of 3-aryl-2-oxazolidinones finally.

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.

Asymmetric Hydrolytic and Aminolytic Kinetic Resolution of Racemic Epoxides using Recyclable Macrocyclic Chiral Cobalt(III) Salen Complexes

New chiral macrocyclic cobalt(III) salen complexes were synthesized and used as catalyst for the asymmetric kinetic resolution (AKR) of terminal epoxides and glycidyl ethers with aromatic/aliphatic amines and water as nucleophiles. This is the first occasion where a Co(III) salen complex demonstrated its ability to catalyze AKR as well as hydrolytic kinetic resolution (HKR) reactions. Excellent enantiomeric excesses of the epoxides, the corresponding amino alcohols and diols (upto 99%) with quantitative yields were achieved by using the chiral Co(III) salen complexes in dichloromethane at room temperature. This protocol was further extended for the synthesis of two important drug molecules, i.e., (S)-propranolol and (R)-naftopidil. The catalytic system was also explored for the synthesis of chirally pure diols and chiral cyclic carbonates using carbon dioxide as a greener renewable C1 source. The catalyst was recycled for upto 5 catalytic cycles with retention of enantioselectivity. (Figure presented.).

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.

Heterogeneous catalytic conversion of glycerol with n-butyl alcohol

The etherification of glycerol with n-butyl alcohol at 140°C in the presence of sulfonated cation-exchange resins and zeolite catalysts in an autoclave reactor has been studied. It has been shown that styrene - divinylbenzene ion-exchange resins are effective catalysts for the production of glycerol n-butyl ethers: the glycerol conversion is about 98% with an n-butyl ether selectivity of about 88 mol % (140°C, 5 h, 5 wt % Amberlyst 36 catalyst, and 10 wt % glycerol in n-butanol). Zeolites Y and β in the H+ form exhibit comparable specific activity (glycerol conversion of no more than 25% under similar conditions) in combination with high selectivity for glycerol di-n-butyl ethers (up to 28%).

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.

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