Synthesis of ethylene glycol diacetate (1,2-diacetoxyethane)

Preparation of ethylene glycol diacetate

Preparation of ethylene glycol diacetate (1,2-diacetoxyethane)

Preparation of ethylene glycol diacetate (1,2-diacetoxyethane)

1-liter, short-necked, round bottom flask, fitted with a reflux condenser is charged with a mixture of 60 g ethylene dibromide, 20 g glacial acetic acid, and 60 g of finely pulverized, freshly fused potassium acetate. The reaction mixture is heated to boiling for 2-3 hours under reflux and the crude glycol diacetate is distilled. The distillate is then further treated with 60 g ethylene dibromide and 80 g fused, finely pulverized, fused potassium acetate, and the mixture, as above, heated to boiling for 2-3 hours. The crude glycol diacetate is then again distilled and purified by distillation using efficient fraction column. Three fractions are collected: < 140° C; from 140-175° C and > 175° C. Fractions from 140-175° C and > 175° C are redistilled separately. The pure ethylene glycol diacetate distills between 180-190° C, the main portion at 186° C. The yield of ethylene glycol diacetate is 70 g. Additional 15 g could be obtained by repeating the synthesis with the fraction collected under 180° C.

The practical methods of organic chemistry, by L. Gattermann, 171, 1909

IUPAC Name

2-acetyloxyethyl acetate

InChI

InChI=1S/C6H10O4/c1-5(7)9-3-4-10-6(2)8/h3-4H2,1-2H3

InChI Key

JTXMVXSTHSMVQF-UHFFFAOYSA-N

Canonical SMILES

CC(=O)OCCOC(=O)C

Depositor-Supplied Synonyms

1,2-Diacetoxyethane, Glycol diacetate, Ethylene diacetate, ETHYLENE GLYCOL DIACETATE, 1,2-Ethanediol, diacetate, 111-55-7, Ethanediol diacetate, Ethylene glycol, diacetate, 1,2-Ethanediol diacetate, Ethylene diethanoate, Aptex Donor H-plus, 2-acetyloxyethyl acetate, Ethylene acetate, Ethylene di(acetate), 1,2-Ethanediol, 1,2-diacetate, NSC 8853, ethane-1,2-diyl diacetate, HSDB 430, EINECS 203-881-1, SBB060701, BRN 1762308, AI3-08223, DSSTox_CID_6880, DSSTox_RID_78235, DSSTox_GSID_26880, CAS-111-55-7, Ethylene diacetin, EGDA, 2-acetoxyethyl acetate, ethyleneglycol diacetate, Ethylene gycol diacetate, AC1Q1LCT, UNII-9E5JC3Q7WJ, 2-(Acetyloxy)ethyl acetate, AC1L1QB8, 9E5JC3Q7WJ, Polyethylene glycol diacetate, SCHEMBL64593, WLN: 1VO2OV1, KSC492Q6L, 2-(Acetyloxy)ethyl acetate #, 525200_ALDRICH, CHEMBL3186227, CTK3J2865, NSC8853, JTXMVXSTHSMVQF-UHFFFAOYSA-N, MolPort-001-790-587, CH3C(O)OCH2CH2OC(O)CH3, Polyethylene glycol 400 diacetate, NSC-8853, Tox21_202083, Tox21_303428, AR-1J1249, DCL000107, ZINC01648272, AKOS015913751, RTR-032366, NCGC00249162-01, NCGC00257469-01, NCGC00259632-01, 27252-83-1, AN-43077, CJ-05930, CJ-26644, LS-68534, M431, TR-032366, E0109, FT-0626327, ST50824009, 4-02-00-00217 (Beilstein Handbook Reference), 3B4-0677, I14-44591, Poly(oxy-1,2-ethanediyl), alpha-acetyl-omega-(acetyloxy)-, InChI=1/C6H10O4/c1-5(7)9-3-4-10-6(2)8/h3-4H2,1-2H

Removed Synonyms

1, diacetate, N-stearoylethanolamine, ETHYLENE GLYCOL ACETATE, CID8121, E2012, Poly(oxy-1,2-ethanediyl), .alpha.-acetyl-.omega.-(acetyloxy)-, 1123-96-2

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