Oxetane

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Structural formula
Structure of oxetane
General
Surname Oxetane
other names
  • 1,3-epoxy propane
  • Trimethylene oxide
  • Oxacyclobutane
Molecular formula C 3 H 6 O
Brief description

colorless liquid

External identifiers / databases
CAS number 503-30-0
EC number 207-964-3
ECHA InfoCard 100.007.241
PubChem 10423
ChemSpider 9994
Wikidata Q418107
properties
Molar mass 58.08 g mol −1
Physical state

liquid

density

0.89 g cm −3 (20 ° C)

Melting point

−97 ° C

boiling point

48 ° C

Vapor pressure
  • 350 h Pa (20 ° C)
  • 528 hPa (30 ° C)
  • 773 hPa (40 ° C)
solubility

soluble in water (681 g l −1 at 25 ° C)

Refractive index

1.3961 (20 ° C)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
02 - Highly / extremely flammable 07 - Warning

danger

H and P phrases H: 225-302 + 312 + 332
P: 210-233-302 + 352-403 + 235
Thermodynamic properties
ΔH f 0

−110.8 kJ / mol

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Oxetane is an organic compound . Oxetane is the simplest representative of the heterocyclic four-rings with an oxygen atom in the ring and is therefore one of the cyclic ethers .

Oxetane is a reactive, colorless, highly volatile liquid.

synthesis

By reacting 3-chloropropyl acetate with potassium hydroxide at approx. 140 - 150 ° C.

Syn Oxetan.png

However, the yield is only a little over 40% because a number of by-products are formed.

Another possibility is to cyclize 3-chloropropan-1-ol with a strong base.

Syn Oxetan2.png

The yield is even lower than in the first reaction.

Another possibility is to produce oxetanes using a Paternò-Büchi reaction .

Reactivity

Lewis acids such as boron trifluoride (BF 3 ) can be added to a non-bonding electron pair on the O atom of the oxetane. Cyclooligomerization then takes place in dichloromethane as solvent. The main product is cyclotrimer 1 :

Synthesis of the oxetane cyclotrimer

Linear polyethers are formed under different reaction conditions, especially in the presence of water.

See also

Individual evidence

  1. ↑ Oxetane data sheet (PDF) from Merck , accessed on January 18, 2011.
  2. ↑ a b c d e f g h i Entry on 1,3-epoxypropane in the GESTIS substance database of the IFA , accessed on December 11, 2019(JavaScript required) .
  3. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-408.
  4. ↑ Entry on 1,2-epoxypropane in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  5. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-24.
  6. ↑ a b C. R. Noller: Trimethylene Oxide In: Organic Syntheses . 29, 1949, pp. 92-93, doi : 10.15227 / orgsyn.029.0092 ; Coll. Vol. 3, 1955, p. 835 ( PDF ).
  7. ↑ a b Theophil Eicher , Siegfried Hauptmann, Andreas Memory: The Chemistry of Heterocycles, Wiley-VCH, 2012, ISBN 978-3-527-32747-8 , pp 45-48.