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Unsaturated Hydrocarbons
71. Preparation of Ethylene from Alcohol (Section 29). - Weigh directly into an 8-inch
test-tube 4 grams of phosphorus pentoxide. Connect the test-tube by means of a closely
fitting cork with a reflux air-condenser; immerse the tube in cold water, and pour 5 cc of
ethyl alcohol slowly into the condenser. The alcohol should be added cautiously in small
portions and the test-tube shaken under water, as much heat is evolved when alcohol comes
in contact with phosphorus pentoxide. Support the test-tube at an angle of about 45 with the
table by means of a clamp, and connect it with a delivery-tube arranged to collect a gas over
water. Heat the tube carefully until the mixture becomes homogenous; then more strongly
until a steady stream of gas is evolved. Collect three 250 cc. wide-mouthed bottles of the
gas, and prepare an explosive mixture of ethylene and air. This can be done by placing 20
cc. of water in a 250 cc. wide-mouthed bottle, covering the latter with a glass plate, inverting
in a pneumatic trough, and displacing the water by ethylene. See the following experiment.
Note. - When sulphuric acid, which is commonly used as a dehydrating agent in the preparation of ethylene, is
employed, the reaction takes place at a temperature very near that at which the alcohol chars; as a consequence,
carbon often separates, the mixture froths badly, and sulphur dioxide and carbon dioxide are formed. The
apparatus for the preparation in this way is described under ethylene bromide (experiment 137, page 103).
72. Properties of Ethylene (Section 30). - (a) Inflammability of ethylene. - Throw a lighted
match into a bottle of ethylene. In order to facilitate the removal of the gas, a stream of water
should be poured into the bottle as the gas burns. Note the color of the flame, and compare
with results obtained when methane was burned. (Explain.)
(b) Explosive mixture of ethylene and air. - Throw a lighted match into the bottle containing
the mixture of ethylene and air.
(c) Ethylene and bromine. - Hood. - Add 2 drops of bromine to a bottle of the gas. (See
experiment 66d, page 44.) Replace the glass cover and shake. When the color of bromine
has disappeared, observe carefully the contents of the bottle. Are there drops of an oil
present? (Eq.) Test the gas in the bottle with moist blue litmus paper. Compare the results
with those obtained with methane.
(d) Ethylene and oxidizing agents. - Dissolve a small crystal of potassium permanganate in
about 20 cc. of water, and add a little of the solution to a bottle of the gas. Replace the cover
and shake. Explain the value of the test, and compare the results with those obtained with
methane. (See experiment 66e, page 44.)
(e) Test for unsaturated compounds in coal gas. - Collect over water a bottle of illuminating
gas. Add a dilute solution of potassium permanganate in portions of 5 cc. to the bottle and
shake. What conclusions can be drawn as to the presence of unsaturated hydrocarbons in
illuminating gas? What are the chief constituents of coal gas? Of water gas? Of what value
using an ammoniacal solution of cuprous chloride which can be made as follows: Heat
together in a test-tube over a flame, a few pieces of copper oxide and metallic copper with
about 10 cc. of dilute hydrochloric acid (sp. gr. 1.1). When the solution becomes colorless,
cool, decant off about 5 cc. of the liquid and add ammonia until the solution is alkaline. Add
this solution to a bottle of the gas; cover the bottle and shake. (Eq.)
Notes. - (a) The acetylene prepared in this way from commercial calcium carbide contains impurities, such as
hydrogen sulphide and phosphine. If the gas is to be used to prepare other compounds, it should be purified by
passing it through a wash-bottle containing a solution of mercuric chloride in hydrochloric acid.
(c) It is easy to obtain an explosive mixture of air and acetylene as the proportion of acetylene in such mixtures
may vary between wide limits, namely, from 3 to 82 per cent by volume. In the case of methane and ethylene,
the limiting volumes are from 5 to 13 per cent of the former and from 4 to 22 per cent of the latter.
(f) This test applies only to compounds containing the C-=CH group; the compounds must contain a hydrogen
atom linked to a carbon atom which is joined to a second carbon atom by a triple bond.