Ethylene Glycol → Ethylene glycol diacetate

HRID 128065

Reaction equation

HRID 128065 reaction equation
BrCC[Te](Br)(Br)[CH2:5][CH2:6][Br:7].O=O.[C:12]([O:15][CH2:16][CH2:17][O:18][C:19](=[O:21])[CH3:20])(=[O:14])[CH3:13].[Br:22][CH2:23][CH2:24][O:25][C:26](=[O:28])[CH3:27].C(Br)C[Br:31].C=C.C(O)CO>C(O)(=O)C>[C:12]([O:15][CH2:16][CH2:17][O:18][C:19](=[O:21])[CH3:20])(=[O:14])[CH3:13].[Br:22][CH2:23][CH2:24][O:25][C:26](=[O:28])[CH3:27].[Br:31][CH:6]([Br:7])[CH3:5]

Participants

11

Reactant 7

HCID 174Ethylene GlycolHCID 977OxygenHCID 6325EthyleneHCID 78391,2-DibromoethaneHCID 8121Ethylene glycol diacetateHCID 135641-Acetoxy-2-bromoethaneHCID 86737622Bis(2-bromoethyl)tellurium dibromide2×

Product 3

HCID 8121Ethylene glycol diacetateHCID 112011,1-DibromoethaneHCID 135641-Acetoxy-2-bromoethane

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  1. customglass tube reactor equipped with a gas inlet and outlet tube
  2. temperatureThe reaction mixture was cooled
  3. custompartition chromagraph (glpc.)

Sources & evidence

ORD record
ord-586e5e10a57d46a2ac260a0067ccd962
Source dataset
uspto-grants-1981_03
Patent number
US04258208

Linked notes

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