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4429 12607 1 PB

1. The document summarizes several attempts to prepare and characterize behenic acid. 2. Behenic acid obtained from hardened oils of various seeds melts at 79.3-79.8°C, lower than acids prepared by reducing erucic acid, which vary from 81-84°C. 3. The document details six methods used to prepare behenic acid, all resulting in acids melting between 79.3-80.0°C after purification, consistent with acids obtained from seed oils.

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Hasheem Ali
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45 views2 pages

4429 12607 1 PB

1. The document summarizes several attempts to prepare and characterize behenic acid. 2. Behenic acid obtained from hardened oils of various seeds melts at 79.3-79.8°C, lower than acids prepared by reducing erucic acid, which vary from 81-84°C. 3. The document details six methods used to prepare behenic acid, all resulting in acids melting between 79.3-80.0°C after purification, consistent with acids obtained from seed oils.

Uploaded by

Hasheem Ali
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© © All Rights Reserved
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A s already pointed out (pp.

40, 49, 58 and 66) the behenic acid


obtained from the hardened oils of rape, mustard, jnmba and T~opmZez~m
ma+ seeds melts s t 79.3'-79.8O: This does not agree with the melting
point given by recent author[tles and attempts have therefore been
made to prepare behenic acid by different methods and see whether
the melting points of different specimens of the acid melted n ~ u c h
above 79*S0.

As early as 1846 Walter ( A i ~ m z L e r1846,


~, 60, 271) gave the melting
point at 52-5 jU,hut in 1S48 Volcker ( I b d . , 1848, 64, 342) gave the
value 76' and this was confirmed by Goldschmidt (K%n Acaid., 1874,
70, 451). In 1Sg4 Talanzeff (J. pr. Chefit., 1894, [Ii] , 50, 72) prepared
the acid by the addition of hydrogen iodide to erucic acid and
subsequent reduction in alcoholic solution with zinc and hydrogen
chloride. The melting point is given as 8q0 in a capillary tube.
Meyer, Brod and Skita (Munalsh., 1913, 34, I 128) prepared behenic
acid by reducing pure erucic acid with hydrogen in the presence of
nickel as catalyst and gave the melting point at 82-84", but state that
with a catalyst which has been used several times a product melting at
7s0 is obtained and that it is impossible to get a product melting at 84"
from this. Flecker and Taylor (1.Chem. Suc., 1922, 121, 1 1 0 2 j
used an acid melting at 91-82' and prepared by reducing erucic
acid and subsequent crystallisation from alcohol, and Toyanla (1. Chem.
Zxd. Jnpnn, 1922, 25, 1053) describes an acid obtained by the same
method as melting at 81-8z0.

It is thus clear that the acid obtained iron: the seeds melts at
a lower temperature than the acid prepared by the reduction of
erucic acid, although the values given for this reduced acid vary
from 81 -84O.

Behenic acid has been prepared by the following methods :-


I. The reduction of brassidic acid melting at 59.5-60'0° and
with an equivalent weight 337 (theory) but unknown iodine value by
three per cent. of nickel deposited on kieselguhr. After four hours at
180" the iodine value fell to 4 and the product was repeatedly crpstal-
lised from acetone. After two crystallisations the melting point was
79-3-79-8" and remained constant after further crystallisation.
2. Kahlbaum's pure erucic acid was twice crystallised from
95 per cent. alcohol and was once crystallised by cooling to rgo to
remove saturated acids. About i o per cent. oi the product was
precipitated as lithium salt, also with the object of removing s a t u ~ a t e d
acids, and the residue was crystallised again from alcohol. T h e acid
melted at 33.5-34.0" and had an equivalent 337. I t was reduced at
180" using a nlckel catalyst and on crystallisatron frorn acetone save a
product nlelting at 79.3-79'80

3. Attempts were made to obtain from Kahlbaum's acid a


product with the correct iodine value (7j) by Holde's (Ar~gew.
Chn,~.,1 9 2 2 , 35, 290) method of fractional precipitation with lithium
acetate. The iodine value obtained for the more soluble portions
was only 71-5, and the behenic acid obtained from this by hydrogena-
tion melted a t 79.3-79'8".
a. -4 fresh specimen of erucic acid obtained from Kahlbaum
had the iodine value 7 5.4 and the solidifying point 33.0: T h i s was
completely hardened, extracted with petloleunl ether to remove nickel
soap and the acid crystallised from 95 per cent. alcohol and acetone
in succession. I t melted at 80° and the solidifying point was
79'2".
5. A sample of brassidic acid with an iodine value 73.8
(theory 75) and a melting point 59.5-60.0" gave on reduction an acid
melting at 79-3-79.8' after two crystallisations frorn acetone.
6. As already stated, the acid obtained by hydrogenating
trierucin to tribehenin, and subsequent hydrolysis melted at
79'5-80.0".

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