Ethylene Glycol → Ethylene glycol diacetate

Participants

Reaction Steps

1.05 g. (2.09 mmoles) of bis(2-bromoethyl)-tellurium dibromide, from Example 2, along with 4.0 g. glacial acetic acid (99.5 percent) was charged to a "Fisher-Porter" 35 ml. glass tube reactor equipped with a gas inlet and outlet tube, a pressure gauge and relief valve and a magnetic stirrer. The mixture was heated at a temperature of 150° C. under 16 psig oxygen with stirring for 1 hour. The reaction mixture was cooled and the products analyzed by gas liquid partition chromagraph (glpc.) showed 3.10 mmoles of ethylene glycol diacetate, 0.79 mmoles of 2-bromoethylacetate, 0.12 mmoles ethylene dibromide and a trace amount of ethylene. Based on stoichiometry that one mole of bis(2-bromoethyl)tellurium dibromide yields two moles of ethylene glycol precursors, i.e., ethylene glycol diacetate, 2-bromoethylacetate and dibromoethane, the mass balance was calculated to be 96 mole percent.

Provenance & Evidence