Author Topic: 3-phenylpropan-1-ol experiment  (Read 385 times)

mumbles

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Re: 3-phenylpropan-1-ol experiment
« Reply #20 on: February 14, 2013, 06:56:33 AM »
For anyone else interested in the electroreduction of cinnamaldehyde  :D Quick question the apparatus section describes a Platinum anode, could this be substituted for another material? With the price of platinum it might be more economical to just buy hydrocinnamyl alcohol.

CVI.—Electrolytic reduction. Part VI. Unsaturated aldehydes and ketones
Herbert Drake Law J. Chem. Soc., Trans. 1912,101, 1030

Cinnamaldehyde.
This substance readily resinifies on reduction in both acid and alkaline medium. The reaction was therefore tried in a nearly
neutral electrolyte (Trans., 1911, 99, 1114). Five grams of cinnamaldehyde, 25 C.C. of alcohol, 20 C.C. of ethyl acetate, 20 C.C. of
water, and 4 grams of potassium acetate were electrolysed with a current of 1 ampere for three hours. A lead cathode was employed,
and a current density of 0.05 amperes per sq. cm. The product was diluted with water, extracted with ether, dried, and fractionated
under diminished pressure. Two fractions were obtained, namely, (I) b. p. 100-200°/25 mm., and (II) b. p. 200-300°/25 mm.
There was also a portion of higher boiling point. Fraction I was treated with a solution of sodium hydrogen sulphite to remove the
unchanged aldehyde. The residue boiled at 235°/760 mm., and was b-phenylpropyl alcohol, the yield being 55%. Fraction II
could not be identified. The following results were obtained in three parallel experiments :

Cathode material ........    Copper     Lead         Lead
Temperature ...............    20-30°     20-30°     40-50°
B-Phenylpropyl alcohol   20%           55%         25%
High boiling fraction       60%         20%         40%

CXLIX.—Electrolytic reduction. I. Aromatic aldehydes
Herbert Drake Law J. Chem. Soc.Trans, 1906,89, 1512

Description of the Apparatus.
Throughout this research the same form of apparatus was used. The cathode compartment consisted of a cylindrical porous pot, having a capacity of 120 C.C. This was thoroughly cleaned by forcing first a dilute solution of sodium hydroxide and then dilute sulphuric acid through the walls to remove the soluble metallic impurities. Such a porous pot was fitted with a trebly-bored rubber stopper carrying a dropping funnel, a short delivery tube, and a short glass tube to hold the electrode. In each case the cathode was bent in the form of a cylinder, and was fixed in position by means of sealing-wax ; it had an area of 17.6 sq. em. on one side. The hydrogen escaping from the apparatus was conducted to a graduated measuring cylinder inverted over water, and the volume read off from time to time. The anode compartment was a beaker about 10 cm. deeper than the porous pot, containing a stout platinum wire to act as anode. Three such sets of apparatus were coupled in series with an adjustable rheostat and twelve accumulators. One piece of apparatus was used as a hydrogen coulombmeter and the other two for reduction purposes, one being a duplicate of the other. In this way the total hydrogen reacting at the cathode could be measured from the difference in the water levels of the coulombmeter and the reduction apparatus. In many cases the product was precipitated during the experiment on to the cathode, but did not interfere with the reaction as is the case in acid solutions.

« Last Edit: February 14, 2013, 07:11:03 AM by mumbles »