General Description
The monomer unit of a thermoplastic resin trademarked Penton.
Reactivity Profile
3,3-BIS(CHLOROMETHYL)OXETANE is a chlorinated ether.
Uses
3,3-Bis(chloromethyl)oxetane is used in preparation of light curing ink and its application.
Safety Profile
Poison by ingestion andinhalation. When heated to decomposition it emits toxicfumes of Cl-.
Synthesis
The general procedure for the synthesis of 3,3-bis(chloromethyl)oxetane from 3-chloro-2,2-dichloromethylpropan-1-ol is as follows:
Step a) Preparation of compound 2: A mixture of 3-chloro-2,2-dichloromethylpropan-1-ol (1.0 g, 5.22 mmol) and potassium hydroxide (0.345 g, 85% purity, 5.22 mmol) in ethanol (2 mL) was heated and refluxed for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL), and filtered to remove the solid generated in the reaction. The filtrate was concentrated to give compound 2 (0.65 g, 80% yield) as a colorless liquid. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 4.47 (s, 4H), 3.95 (s, 4H).
Purification Methods
Shake it with aqueous NaHCO3 or FeSO4 to remove peroxides, separate, dry with anhydrous Na2SO4, then distil it under reduced pressure from a little CaH2 [Dainton et al. Trans Faraday Soc 56 1784 1960, Farthing J Chem Soc 3648 1955]. The 3,3-bis(phenoxymethyl) derivative is described below. [Beilstein 17 III/IV 68.] Lachrymatory.
References
[1] Patent: US2005/282826, 2005, A1. Location in patent: Page/Page column 28-29
[2] Patent: KR101592370, 2016, B1. Location in patent: Paragraph 0204; 0205; 0209-0211
[3] Journal of the Chemical Society, 1955, p. 3648,3651
[4] Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen, 1940, vol. 2, # 5, p. 3,16
[5] Kogyo Kagaku Zasshi, 1956, vol. 59, p. 77
