bis(dichloromethyl) ether

Main page (Russian)

Search in database (English)

Properties of substance:

bis(dichloromethyl) ether

Synonyms:

dichloro(dichloromethoxy)methane

Group of substances:

organic

Empirical formula (Hill's system for organic substances):

C₂H₂Cl₄O

Structural formula as text:

Cl2CHOCHCl2

Synthesis 1:

Reference: Evans, L., & Gray, R. Preparation of Certain Polychlorodimethyl Ethers / Journal of Organic Chemistry. - 1958. - Vol. 23, No. 5 pp. 746 [doi: 10.1021/jo01099a602]

ClCH₂OCHCl₂ + Cl₂ → Cl₂CHOCHCl₂ + HCl

A 2-liter, 3-necked flask which was equipped with a mechanical stirrer, condenser and ice trap, thermometer, and sintered-glass disk inlet tube was charged with 284 g. (1.9 moles) chloromethyl dichloromethyl ether and 616 g. (4.0 moles) carbon tetrachloride. The solution was heated to reflux and chlorine was bubbled in at a rate of 114 ml./min. until 81 g. (1.15 moles) had been introduced. The heat of reaction maintained the system at reflux. By fractionation at reduced pressures, 63 g. (0.34 mole) (29.6% yield) of bis(dichloromethyl) ether was obtained having b.p. 143°, n(20, D) 1.4728 and d(30/4) 1.558.

Anal. Calcd. for CHCl2OCHCl2: mol. wt., 183.9; Cl, 77.13. Found: mol. wt., 190; Cl, 76.4.

Only one product resulted from this reaction whereas two products are possible. Since neither of the two expected products is reported in the literature, the identity of the product was confirmed by mass spectrometer and infrared pattern. The mass pattern showed relative peak heights at 83, 85, and 87 of 1.00:0.64:0.116 which is in good agreement with the values expected for CHCl2 based on the relative abundance of the chlorine isotopes. The ratios of the heights of the 117, 119, 121, and 123 peaks are 1.00:4.67:4.00:1.17. These values are not in agreement with the heights expected for a CCl3 group which should be 1.0:1.0:0.3:0.04. The infrared pattern as interpreted by Dr. W. H. Calkins is in agreement with the pattern to be expected for the sym-tetrachloro derivative. Furthermore, the relative areas from a gas chromatogram indicated that the sample was about 95% pure.

References:

Your requests if no data into database