2-hydroxyethyl Esters Research Articles

Synthesis of 2-Hydroxyethyl Esters from Castor Oil as Lubrication Bio-Additive Candidates for Low-Sulfur Fossil Diesel

The present work aims to study the synthesis of 2-hydroxyethyl esters from castor oil and its lubrication properties, promising as a lubrication bio-additive in low sulfur diesel fuel. This compound has been successfully synthesized from castor oil and ethylene glycol. The oil to ethylene glycol molar ratio was adjusted to 1:10, and the catalyst loading was used at 9% mole oil. Then, the mixture was refluxed for 5 h. The product components were characterized using GC-MS. The standard ASTM method was used to study the kinematic viscosity and lubrication. The product was dominated by 2-hydroxyethyl esters (94.16%), di-ester (1.12%), and cyclic ester (1.92%). The analysis of friction coefficient and wear scar diameter (WSD) using High-Frequency Reciprocating Rig (HFRR) shows the coefficient of friction and WSD of the product better than reference diesel fuel. From the results of this study, the 2-hydroxyethyl ester of castor oil, especially 2-hydroxyethyl ricinoleate, is the main responsible for the lubricating properties. Thus, 2-hydroxyethyl esters of castor oil can be proposed as an alternative bio-additive to improve the lubrication of low-sulfur fossil diesel fuels.

Furfural-Based Modification of PET for UV-Blocking Copolymers with Decreased Oxygen Permeability

2,2′-Bifuran-5,5′-dicarboxylic acid (BFDCA), a highly promising biobased diacid monomer, was used to modify poly(ethylene terephthalate) (PET) to obtain copolyesters with increased biocarbon content and improved properties compared with PET. Antimony-catalyzed copolymerization of the bifuran and terephthalate 2-hydroxyethyl esters was used to afford the PETBF copolymers. When compared against PET, these random copolymers with 5, 10, or 15 mol % of the bifuran comonomer in the feed (relative to the total amount of the starting esters) showed a slightly elevated glass transition range, higher tensile moduli, enhanced oxygen gas barrier properties, and superior UV blocking while maintaining good transparency otherwise. Based on our results, PETBF copolyesters seem to have promise as materials with enhanced properties that are desirable in advanced packaging applications.

A facile synthesis of ( S)-felodipine

A short and facile synthesis of ( S)-felodipine was developed starting from ( R)-glycidol as the source of the chiral auxiliary. 2-Hydroxyethyl esters were found to undergo selective transesterification reactions in the presence of other esters. This selective transesterification reaction was applied to the synthesis of ( S)-felodipine through selective substitution of the 2-hydroxyethyl group possessing chiral ester with sodium methoxide.

ChemInform Abstract: Selective Lewis Acid Complexation of 2-Hydroxyethyl Esters Using Competitive Diels-Alder Reactions as a Mechanistic Probe.

Abstract Competitive Diels–Alder reactions involving ethyl acrylate, 2-hydroxyethyl acrylate and 2-methoxyethyl acrylate indicate that certain Lewis acids (e.g. EtAlCl2) selectively complex to the 2-hydroxyethyl ester group. Studies using ethyl 2-hydroxyethyl fumarate support these findings. 13C NMR spectroscopy provides some evidence regarding the nature of the interactions between 2-hydroxyethyl esters and EtAlCl2. The influence of EtAlCl2 on the level of diastereocontrol observed in the Diels–Alder reactions of (2R∗,3R∗)-2-(3-hydroxy)butyl acrylate is described.

Biodegradability of aromatic building blocks for poly(ethylene terephthalate) copolyesters

A biodegradability study of several aromatic building blocks used for the preparation of poly(ethylene terephthalate) copolymers of technical interest has been carried out. They include the dimethyl esters of terephthalic, 5-nitroisophthalic, and nitroterephthalic acid, as well as the 2-hydroxyethyl esters of the first two mentioned acids. Biodegradability was first evaluated on solid agar for a number of culture collection strains. Only 7 out of the 24 assayed strains showed degrading activity on some substrates. The degrading microorganisms were then isolated from environmental samples using an enrichment culture technique. Most of the environmental isolates showing degrading capability belonged to the genus Pseudomonas or Bacillus. Biodegradation with commercial lipases, esterases and proteases showed that most of the 16 tested enzymes degraded some of the substrates.

Selective Lewis Acid Complexation of 2-Hydroxyethyl Esters using Competitive Diels–Alder Reactions as a Mechanistic Probe

Competitive Diels–Alder reactions involving ethyl acrylate, 2-hydroxyethyl acrylate and 2-methoxyethyl acrylate indicate that certain Lewis acids (e.g. EtAlCl 2) selectively complex to the 2-hydroxyethyl ester group. Studies using ethyl 2-hydroxyethyl fumarate support these findings. 13C NMR spectroscopy provides some evidence regarding the nature of the interactions between 2-hydroxyethyl esters and EtAlCl 2. The influence of EtAlCl 2 on the level of diastereocontrol observed in the Diels–Alder reactions of (2 R ∗,3 R ∗)-2-(3-hydroxy)butyl acrylate is described.

Selective complexation of 2-hydroxyethyl esters using lewis acids

Competitive Diels-Alder reactions between ethyl acrylate and 2-hydroxyethyl acrylate (1,3-cyclopentadiene, CH2Cl2, 0°C) in the presence of a variety of Lewis acids indicate that selective complexation of the 2-hydroxyethyl ester can be accomplished, most notably using EtAlCl2. Further Diels-Alder reactions using ethyl 2-hydroxyethyl fumarate support these findings. 13C NMR studies provide direct evidence for the nature of the interactions between 2-hydroxyethyl esters and EtAlCl2.

Evidence for the formation of 2-hydroxyethyl esters by reaction of fatty acids with diazomethane in diethyl ether

Alkylation of long-chain saturated, unsaturated and unsaturated hydroxy fatty acids with ethereal diazomethane was investigated. Upon reaction with ethereal diazomethane, fatty acids dissolved in a minimal volume of diethyl ether/methanol (9:1) produced 98–99% methyl ester. Omission of methanol caused the formation of 10–40% side products. The side products from octadeca-9,12-dienoic and 13-hydroxy-octadeca-9,11-dienoic acid were isolated and conclusively identified as 2-hydroxyethyl esters by 13C-NMR spectroscopy and mass spectrometry.

Synthetic studies with carbonates. Part 6. Syntheses of 2-hydroxyethyl derivatives by reactions of ethylene carbonate with carboxylic acids or heterocycles in the presence of tetraethylammonium halides or under autocatalytic conditions

Reactions of ethylene carbonate (1a) with a variety of carboxylic acids catalysed by tetraethylammonium halides gave the corresponding 2-hydroxyethyl esters along with the diesters arising from disproportionation of the former products induced by the quaternary ammonium halides. Formation of the disproportionation products could be minimized by use of a short reaction time. The autocatalytic reactions of (1a) with strongly acidic carboxylic acids at elevated temperature gave ethylene glycol diesters selectively. Reaction mechanisms are discussed. Reactions of cyclic carbonates such as (1a) and propylene carbonate(1b) with acid anhydrides or active acyl compounds such as p-nitrophenyl acetate in the presence of tetraethylammonium iodide gave alkylene glycol diesters or 2-acyloxyalkyl aryl ethers in high yields. An attempt to extend this reaction to cyclohexane-1,2-diyl carbonate was unsuccessful, but a reaction with 1,2-epoxycyclohexane succeeded; this enabled us to examine the stereochemistry of the reaction. Finally, N-2-hydroxyethylation of a series of heterocyclic compounds having acidic imino hydrogen atoms was performed, both with tetraethylammonium iodide as catalyst and without a catalyst.

Liquid chromatography of benzenedicarboxylic acids and their 2-hydroxyethyl esters on silica gel

Liquid chromatography of benzenedicarboxylic acids and their 2-hydroxyethyl esters on silica gel

Kinetics and mechanism of the reaction of aromatic carboxylic acids with ethylene oxide in protic and aprotic dipolar solvents in the presence of tertiary amines

Aromatic carboxylic acids react with ethylene oxide in the presence of tertiary amines as catalysts both in protic and in aprotic solvents to give the corresponding 2-hydroxyethyl esters by the amine- and acid-catalysed parallel reactions. In protic solvents, the acid-catalysed reaction is first-order in both the acid and ethylene oxide and its rate correlates with the acid strength by Br0nsted equation with the constant corresponding to a value of 0-62. The parallel aminecatalysed reaction of the acids with x>K^ ^ 3-99 is in these solvents first-order in both ethylene oxide and the amine, and the Br0nsted ci.2 constant has a value of 0-34. In the amine-catalysed reaction of the acids with pAT^ 318 there is a change in the nature of the rate-deter­ mining step; the reaction of the acids with pisTg ^318 proceeds solely with the acid participating in the rate-determining step of the amine-catalysed reaction which is first-order in the acid, ethylene oxide, and tertiary amine. Of the two parallel reactions occuring in protic solvents, the amine-catalysed one has the higher activation energy and by about 6 to 7 orders of magnitude higher values of the preexponential factor. In aprotic dipolar solvents the acid-catalysed reaction is first-order in both the acid and ethylene oxide, and the Bronsted constant a'^ has a value of 096. The amine-catalysed reaction is in this case first-order in the acid, ethylene oxide, and tertiary amine, and its kinetics does not change with the acid strength of carboxylic acids; the Bronsted constant a'2 has a value of 0-60. The Hammett reaction constants Q2, Q'I and Q'2 have the same values as the respective aj, 0.2, c/ and constants. The previous work of this series was concerned with the kinetics and mechanism of reactions of acetic acid, monochloro- and dichloroacetic acids with ethylene oxide catalysed with tertiary amines and carried out in alcohols as solvents^. In the work it was suggested that under the condi­ tions used ethylene oxide is consumed by both the acid-catalysed and parallel tert-amine-catalysed bimolecular nucleophilic substitution reactions. The reactions of ethylene oxide were accompanied by side reactions which especially in the case of the chloro-substitut ed acids led to formation of considerable amounts of by-products. This circumstance left some doubt concerning the validity of the kinetic dependences obtained for the whole region of conversions of the carboxylic acids. The results reported in the above-mentioned study allowed also to draw only qualitative conclusions about the relationship between the rate of the ethylene oxide reaction with carboxylic

Separation of alkali metal carboxybenzenesulphonates and their 2-hydroxyethyl esters on sephadex LH-20 gel

Mixtures of alkali metal carboxybenzenesulphonates and their 2-hydroxyethyl and bis(2-hydroxyethyl) esters, obtained by esterification of the carboxybenzene-sulphonates with ethylene glycol at elevated temperatures, were readily separated by chromatography on Sephadex LH-20 gel at pH 8.5 by using potassium dihydrogen orthophosphate-disodium hydrogen orthophosphate buffer as eluent.

Synthesis of deoxyuridylyl-(3'→5')-ribonucleoside [P-(2-hydroxyethyl) esters

Synthesis of deoxyuridylyl-(3'→5')-ribonucleoside [P-(2-hydroxyethyl) esters