Carbon Dioxide → Propylene Oxide

HRID 1980001Notes

Reaction equation

O.[CH2:2]=[CH:3][CH3:4].[C:5](=[O:7])=[O:6].[Cl-].Cl.[CH2:10]1[O:13][CH:11]1[CH3:12].Cl.[OH-].[Na+]>C(C(C)=O)C>[CH2:10]1[O:13][CH:11]1[CH3:12].[CH3:10][C:11]([CH3:12])=[O:13].[C:5]1(=[O:13])[O:7][CH:3]([CH3:4])[CH2:2][O:6]1

Participants

Conditions

Temperature: -78 °C

Procedure

4.0 g thallic oxide (8.8 mmoles) and 30 g water (1.7 moles) were added to a 300 cc Autoclave Engineers stainless steel Magnedrive Autoclave. The autoclave was cooled to -78° C. and 40 g propylene (0.95 mole) and 100 g carbon dioxide (2.3 mole) were introduced. The autoclave was then heated to 100° C. for 1.0 hour to reach a total pressure of 196.8 kg/cm2. The autoclave volatiles were then vented into a methyl ethyl ketone solution followed by a 0.10 M megnesium chloride-hydrochloric acid scrubber which trapped the propylene oxide. The excess hydrochloric acid was titrated with 0.10 M sodium hydroxide. The organics remaining in the aqueous solution were measured by standard gas chromatographic techniques. The analysis showed 1.01 mmoles propylene oxide (48% yield), 0.71 mmoles acetone (34% yield) and 0.10 mmoles propylene carbonate (5% yield). 2.1 mmoles of thallous bicarbonate (24% conversion) were detected in the water solution by atomic absorption techniques. The pH of the solution was measured to be 8.1. The yields of oxidized propylene products in this and the following examples are based on the thallic compounds reduced to the thallous state. The conversions of thallic reduction to thallous are based on the starting quantity of thallic compound.

Workup

temperatureThe autoclave was then heated to 100° C. for 1.0 hour

Sources & evidence

ORD record: ord-2e776b22802444ce9da4692ac97d9664
Source dataset: uspto-grants-1984_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04483996

Reaction notes

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