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Azeotropes of epichlorohydrin 112
Binary systems
|
| Other component |
Azeotrope data |
Formula |
Name |
B.P. °C |
B.P. °C |
Wt. %
Epichlorohydrin |
| CCl3NO2 |
Trichloronitromethane |
111.83 |
106 |
| C2CI4 |
Tetrachloroethylene |
120.8 |
110.12 |
515 |
| C2H402 |
Acetic acid |
118.5 |
115.05 |
655 |
| C2H4BrCl |
1-Bromo-2-chloroethane |
106 |
103.5 |
17 |
| C3H6O |
Allyl alcohol |
96.95 |
95.8 |
22 |
| C3H8O |
Propyl alcohol |
97.2 |
96 |
23 |
| C4H9Br |
1-Bromobutane |
101.6 |
100 |
- |
| C4H9l |
1-lodobutane |
130.4 |
<115 |
<92 |
| C4H9l |
1-lodo-2-methylpropane |
120.8 |
111 |
47 |
| C4H10O |
n-Butyl alcohol |
116.9 |
112 |
57 |
| C4H10O |
Isobutyl alcohol |
108 |
105 |
39.5 |
| C5H11Br |
1-Bromo-3-methylbutane |
120.2 |
110.1 |
>52 |
| C5H12O |
lsoamyl alcohol |
131.8 |
115.35 |
81 |
| C6H120 |
tert-Amyl alcohol |
102 |
100.1 |
30 |
| C6H12O2 |
Isoamyl formate |
123.6 |
116.2 |
- |
| C6H12O2 |
Isobutyl acetate |
117.2 |
<115 3 |
>50 |
| C6H12O2 |
Ethyl butyrate |
121.5 |
115.75 |
75 |
| C6H12O2 |
Methyl isovalerate |
116.3 |
115 |
45 |
| C7H8 |
Toluene |
110.75 |
108.4 |
29 |
| C8H18 |
n-Octane |
125.8 |
114.5 |
80 |
| C8H18 |
2,5-Dimethylhexanp |
109.2 |
107 |
25 |
|
The ternary system epichlorohydrin - tetrachloroethylene-l-iodo-2-methylpropaneforms a minimum boiling mixture at 120.0°C
112.
See the indicated references for the cryoscopic 4 and ebullioscopic 1 78 behavior of epichlorohydrin in benzene, the dissociation and electrical conductivity of solutions of tetraethylammonium iodide and tetrapropylammonium iodide in epichlorohydrin 243, and the electrical conductivity of solutions of iodine and of mercuric chloride in epichlorohydrin 205.
levo-Epichlorohydrin: Boiling point, 92-93°C at 360 mm. (racemization occurs on distilling at atmospheric pressure); d, 1.2007;
For other physical data on epichlorohydrin see references 14, 114.
Typical properties of commerical epichlorohydrin
|
| Purity |
99.5% by weight epichlorohydrin |
Specific gravity,
at 20/20°C |
1.1 81 to 1.184 |
| Color |
15 platinum cobalt (Hazen) standard |
| Water |
0. 1 % by weight |
|
Chemical properties 14, 114, 206
Both the epoxy group and the chlorine atom of epichlorohydrin are highly reactive. In most of its reactions, however, the compound behaves primarily as an epoxide, initially combining through the epoxy group with subtances containing an active hydrogen atom and with numerous other diverse compounds to form derivatives of glycerol a-monochlorohydrin. This is true even of its behavior toward such types of substances as nitrogen bases, metal alkoxides, and organic acid salts which normally effect direct metathetical replacement of an active organic halogen atom. With such reagents the chlorine atom may be eliminated as hydrogen chloride in a subsequent step of the same or an independent reaction to form glycidol derivatives-, these in turn undergo the additive reactions typical of epoxy compounds. Epichlorohydrin thus serves as a convenient and practical intermediate for the synthesis of derivatives of a-monochlorohydrin, glycidol, and glycerol, and particular attention is given to representative reactions leading to such products.
Reactions with inorganic substances
With oxidizing and reducing agents. Epichlorohydrin is converted to ß-chlorolactic acid 195 on warming with nitric acid. This product is likewise obtained by oxidation of a-monochlorohydrin 134.
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