2-hydroxyethyl octanoate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Three fractions containing 68.6 to 97.8% of 2-hydroxyethyl caprylate were obtained by heating caprylic acid (1.25 mol; 180 g) with ethylene glycol (8.27 mol; 513.5 g) to boiling temperature for 5 hours and gradual distillation; the overall yield of 2-hydroxyethyl caprylate was 61.3%. In addition to 2-hydroxyethyl caprylate, ethylene dicaprylate was formed from 21% of caprylic acid. In a similar experiment, the reaction mixture after 7 hours of heating was first extracted with benzene and the benzene extract with water, instead of direct distillation. Caprylic acid was consumed in 60.6% for 2-hydroxyethyl caprylate, whereas ethylene dicaprylate resulted from 21.5% of acid; distillation gave fractions of raw product containing 97.6 to 98.5% of 2-hydroxyethyl caprylate. Further procedure was carried out according to example 1. were obtained for 5 hours gradual distillation In addition to 2-hydroxyethyl caprylate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Anhydride of caprylic acid (0.477 mol; 129 g) was dropwise added into boiling dry ethylene glycol (3.16 mol; 196 g) and the mixture was refluxed for further 4 hours. The mixture was cooled, extracted twice with benzene (100+20 ml), benzene was evaporated in a rotation evaporator, and the residue was distilled. 2-Hydroxyethyl caprylate was obtained in the yield of 142.75 g (159% of theory), which is the evidence that almost 2/3 of caprylic acid formed was esterified with glycol under the experimental conditions. The raw fractions had purity 88.9 to 97.5% of 2-hydroxyethyl caprylate. Further procedure was carried out according to example 1. the mixture was refluxed for further 4 hours The mixture was cooled extracted twice with benzene (100+20 ml), benzene was evaporated in a rotation evaporator the residue was distilled

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Capryloyl chloride (0.602 mol; 98 g) was dropwise added during 1.5 hour into a mixture of ethylene glycol (3 mol; 186 g) and pyridine (0.6 mol; 47.4 g). The mixture was further stirred for 2 hours at laboratory temperature, allowed to stand overnight, and threetimes extracted with benzene (100+50+25 ml). The benzene extract was shaken with a 10% aqueous solution of NaHCO3 (2×30 ml) and water and benzene was evaporated in a rotation evaporator. Distillation of the residue gave 4 raw fractions with purity 79.9 to 97.9% at the overall yield of 2-hydroxyethyl caprylate 79.5%. Further procedure was carried out according to example 1. to stand overnight threetimes extracted with benzene (100+50+25 ml) The benzene extract was shaken with a 10% aqueous solution of NaHCO3 (2×30 ml) and water and benzene was evaporated in a rotation evaporator Distillation of the residue

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Sodium caprylate (2 mol) was prepared by neutralization of caprylic acid (2 mol; 288.4 g; 317.4 ml) in 750 ml xylene with sodium hydroxide (2 mol; 80 g) in water (160 ml). The reaction mixture was freed of water and then heated with chloroethanol (2.1 mol; 170 g; 204.4 ml) with addition of 2-ethoxyethanol (1000 ml) as a solvent under reflux for 28 hours. The precipitated NaCl was filtered off and washed with 2-ethoxyethanol. The filtrate was distilled and 66% of 2-hydroxyethyl caprylate was obtained; b.p. 141° C./266 Pa. Elemental analysis for C10H20O3 theory: 63.79% C, 10.71% H; found: 63.54% C, 10.93% H. The structure was confirmed by infrared and 13C--NMR spectroscopy. Further procedure was carried out according to example 1. under reflux for 28 hours The precipitated NaCl was filtered off washed with 2-ethoxyethanol The filtrate was distilled

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-hydroxyethyl caprylate (HEC) (1 mol; 188.3 g) in pyridine (1.25 mol; 98.9 g; 100.7 ml) was added under continuous stirring at 5°-10° C. into a solution of freshly distilled acryloyl chloride (1.12 mol; 101.4 g) in benzene (300 ml). The mixture was further stirred for 2 hours at the reaction temperature, extracted with 800 ml of 2% hydrochloric acid, the emulsion formed was broken by addition of ether and the aqueous layer was repeatedly extracted with ether until the reaction on capryloyloxyethyl acrylate was negative. The combined ether extracts were washed with water, solution of potassium hydrogencarbonate (KHCO3), and water and dried with magnesium sulfate (MgSO4). Ether was removed by distillation under normal pressure and the product was distilled after addition of octylpyrocatechol as an inhibitor. The overall yield of raw product was 74.9%. The obtained fractions contained 60 to 93% of capryloyloxyethyl acrylate. The product with purity 99.8% was obtained by redistillation; b.p. 111° C./66.7 Pa. Elemental analysis for C13H22O4 theory: 64.44% C, 9.15% H; found 64.23% C; 9.41% H. The infrared and 13C-NMR spectra proved the expected structure. extracted with 800 ml of 2% hydrochloric acid the emulsion formed the aqueous layer was repeatedly extracted with ether until the reaction on capryloyloxyethyl acrylate The combined ether extracts were washed with water, solution of potassium hydrogencarbonate (KHCO3), and water dried with magnesium sulfate (MgSO4) Ether was removed by distillation under normal pressure the product was distilled after addition of octylpyrocatechol as an inhibitor The product with purity 99.8% was obtained by redistillation