TRIMETHYLENE OXIDE

Chemical properties

CLEAR COLOURLESS LIQUID

The Uses of TRIMETHYLENE OXIDE

Trimethylene oxide useful for the synthesis of 3-substituted propanols by reaction with Grignards or organolithiums in the presence of CuBr.

Definition

ChEBI: A saturated organic heteromonocyclic parent that is a four-membered ring comprising of three carbon atoms and an oxygen atom.

General Description

Clear, colorless liquid with an agreeable aromatic odor.

Air & Water Reactions

Highly flammable. Water soluble.

Reactivity Profile

TRIMETHYLENE OXIDE reacts with Grignard reagents and organolithium compounds. TRIMETHYLENE OXIDE is also incompatible with oxidizing agents and strong acids. . An explosion occurred when propylene oxide was added to epoxy resin. Polymerization was catalyzed by amine accelerator in the resin [Bretherick 1995]. Propylene oxide and sodium hydroxide base-catalyzed the polymerization of the former, causing ignition and explosion of a drum of the crude product. [Combust Sci. Technol., 1983].

Fire Hazard

TRIMETHYLENE OXIDE is flammable.

Safety Profile

Moderately toxic by subcutaneous route. May be narcotic in high concentrations. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes

Purification Methods

Distil oxetane twice from sodium metal and then fractionate it through a small column at atmospheric pressure, b 47.0-47.2o. It can also be purified by preparative gas chromatography using a 2m silica gel column. Alternatively, add KOH pellets (50g for 100g of oxetane) and distil it through an efficient column or a column packed with 1/4in Berl Saddles with the main portion boiling at 45-50o being collected and redistilled over fused KOH. [Noller Org Synth Coll Vol III 835 1955, Dittmer et al. J Am Chem Soc 79 4431 1957, Beilstein 17 H 6, 17 I 3, 17 II 12, 17 III/IV 13, 17/1 V 11.]