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. Dec. 17, 1946.
Filed Aug. 1, 1942
OR AR oma r/c .nu 15N r
17, v1946
. 2,412,818
Joseph John4 Lovas, Ridgewood, and James F.
Loughlin, New York, N. Y.
Application August 1,_ 1942, Serial No. 453,294
2 Claims. (Cl. 260-97.5)
2 ;
The_invention relates in general _to the prepa,
cases where'the original fatty acidwas unsatu
ration of waxes from fatty acids, and in particu
lar to a process of preparing waxes from the fatty
rated. In cases where the original fatty acid
was saturated, a solvent such as benzene, toluene
acids present in mixed ’fatty and rosin acids pre
pared from kraft pulp millwaste soap.
~_ The mixed ’acids contain varying percentages
or xylene is required. During _the step of sepa
rating the fatty acid‘waxes from the unreacted
rosin acids, any solvent may be-used in .which
of _fatty-acids androsin acids. The fatty acids
all the constituents are soluble „when hot and`
consist principally oi’ unsaturated fatty acids such
in _which solvent only thafatty ‘acidi waxes. are
as oleic acid with smaller proportions of linoleic
. acid and linolenic acids.
substantially insoluble when cold. ‘
The general objectïof the invention -is to pre
A water solution containing _69.3% vethylene di
amine was used in performing this synthesis, but i
pare waxes from the above unsaturated fatty acids
the theoreticalv quantity of> any reasonable con
and also from saturated fatty acids._
centration inV water may be usedfsince water is
Al specific object ofthe invention is to prepare
evaporated from the mixture during the reac-_
waxes from the fatty acids and to separate these 15 tion.‘
f-waxes from the rosin lacid constituents of the
For a further understanding" of the nature and
“mixed acids.”-'
objects of the invention, reference should be had
to the accompanying drawing, and to the follow
ing examples _which are given ‘merely to further
A further objectof this invention is to provide
~ a process for the searation of the fatty and rosin
acid constituents in a mixture of fatty acid con
stituents and rosin acid constituents.
20 'illustrate the 4invention and are _not to be con
strued in a limiting sense.
.Other objects 'will in part be obvious and will
` in part hereinafter»appear.` A
We have now found that waxes can be prepared
The drawing illustrates diagrammaticallythe
l set-up of suitable apparatus. VAl reaction vessel
which will be heated, receives-i the Imixed fatty
from saturated vand _unsaturated fatty acids by 25 and rosin acids, or tall oil, and the vessel'also
reacting these acids ywith ethylene diamine ac
receives ethylene diamine and discharges waterv
cording to the following reaction, using oleic acid
vapor. The treatedl mixture, after completion bf
the reaction _in the reaction vessel is completely
as anexample:`
dissolved in a, suitable heated‘solvent.. This may
be done in the reaction vessel or` in a separate
vesselsuch as the crystalli'zer. VThis heated solu
We have -found that _when mixtures of fatty
tion is then cooled sumciently-Íto’cause the fatty
and rosin acids are _treated at an elevated tem
acid wax or waxes to crystallize while substan
perature- with ethylene diamine in quantity suiiif
cient only to react with the fatty acids, the fatty 35 tially all of the other constituentsremain in solu
tion in the- solvent. The” crystallized wax (or
acidcomponents will react to form waxes, while
waxes) is then separated and recovered from
'the rosin acid components will not. The resulting
solvent solution, as by theïñlter shown. The
mixture comprises a fatty acid wax and rosin
filtrate may be led _to a still‘orfevaporator, the
acid. We have found that the rosin acids may
be extracted from the fatty wax _by a suitable 40' solvent evaporated',condensedand- run back for
re-use in the process. ` Upóneevaporation of the
solventV such'as methanol for unsaturated fatty
solvent from the filtrate, any ¿rosingacids or _other
acid waxes. The wax thus obtained is practically
constituents not previously removed, will _be re-,Í __
4free of rosin acids.,‘
. The invention accordingly comprises the sev
eral steps and the relation of one or more of such
'steps with respect to each of the others thereof, `
which will'be exemplified in the process herein
covered as end-product. >
Example ¿I
10o -grams .of a. mixed fattyffand` rosin acidi@
with an acid number of 184 and _a rosin acid num-_
after disclosed, and the scope of the invention '
ber of '12.5' was heated for a'iperiod lof .4 hours >at a
will be indicated in the claims.
In carrying out the process
the invention, 50 temperature of 180°-200° , Cri with _8.65 gm. of a
the fatty acids may be saturate 'or unsaturated,
69.3% solution ethylene diamine'in water. This i
operation was carried out in_a25700` cc. round bot
y and may .be combined with or free of rosin acids.
During the step of separating the fatty
tom nask nttea with ajslass‘iube- connecting
waxes from the unreacted rosin acids, -any suit
with a water cooled condenserlleading downward
able 'solvent such as methanol may be used in 5,5 to a collecting vessel.` During’fthe heating period,
6.4 `grams of distillate were collected. -'I'his dis-IV '_
tillate was accounted for as follows:
. chilling, the stearic acid wax compound was very
- readily crystallized. It was »purified by recrystal
lizing from fresh xylol and filtered out. Benzol '
and toluol are> entirely suitable.
Water from 69.3% ethylene diamine ..-__«___ 2.65
65.8% of' the
crude wax wasl recovered as stearic acid wax
Water from the reaction\_-_v _____________ __ 2.59
- Distillate from other sources _________ -..__ 1.16
compound and.34.2% was recovered from the ñl
After allowing the product to cool, 100.2 grams of
' trate as rosin acids.
a hard brown wax was obtained. l
. genation of the mixed fatty and rosin acids will
It will be understood that the degree of hydro
In order to separate the fatty acid waxes pro
duced from the unsaturated acids present in the
mixture, from‘the -unreacted rosin acids in the
crude wax, the crude mixture was entirely dis-,
solved in 100 cc. of anhydrous methanol at 50°
C. On chilling, a light brown wax was crystal
have relation upon the hardness of the recovered
fatty acid Wax', and that for recovery of wax acid
wax with a lower melting point will not be com_
. pletely hydrogenated.
Since certain changes may be made in carry
ing out the above process without departing from
lized and filtered from a dark brown filtrate. By
the scope of the invention, it is intended that all
recrystallizing from successive 90, 75, 50, 50 and
matter contained in the above- description shall
25 cc. portions of methanol, 38 grams of a white
be interpreted asillustrative-and not in a limiting
wax was prepared:
sense. For example, the prescribed temperatures
Melting point of wax=110°-115° C.
20 and times of reaction may be varied under rea
Iodine value of wax=89.9 ,
sonable limits. . However, simultaneously reduc
ing the specified preferred temperature,-thereby
increasing the time of reaction, and raising the
It was found thatthis unsaturated fatty acid
wax was likewise soluble in warm C014 and in
warm hexane.
temperature substantially above 200° C. may re
25 sult in decomposition. - The temperature range
Example II
and time of reaction are related and subject to
variation over the ranges given in the examples,
and which are preferred. While in the examples
50 grams of tall oil with a fatty- acid content
of 47.7% and a rosin acid content of 44.2% were
heated for a period of 6 hours at a temperature
of about 18W-200°» C., with 3.33 grams of ethylene
diamine. This operation was carried out in the
the preferred, temperature range of 180°-200° C.
was specified, the temperature Amay be reduced to
about 150° C. (this however, requiring a longer
_ time for the reaction) or the temperature may be
ing the heating period 1.9 grams of distillate re
raised to about 225° C. and correspondingly re-`--
' same equipment as was used in Example I.
duclng the time of reaction.
.sulted and was eliminated. After cooling and
It is also to be understood that the following ‘
crystallizing from methanol, 51.0 grams of a 35
~ brown wax was obtained.'
claims are intended to cover all the generic and
This crude wax was
'also quite hard. A white unsaturated fatty acid »
wax similar to_that prepared from the mixed acids
in ExampleI was prepared from the crude mix
specific features of the invention herein de
scribed, and all statements of the scope of the
invention, which as a matter of language might
40 be said to fall therebetween.
ture by crystallizing from methanol.
Having described our invention, what we claim
and desire to _secure by Letters Patent is as fol
Example 1H
50 grams of pure stearic acid were heated for
_1. A process for separating the fatty acid and
a period of 6 hours at a temperatureofabout 180°
C.-200° C., with 7.65 grams of ethylene diamine. _ 45 rosin acid components of acids derived from the
During the heating period, 4.3 grams of distillate
hydrolysis of kraft pulp mill soap which com
were collected.> After dissolving the mixture in
prises the steps of : reacting the mixed. acids with
warm xylol followed by cooling, 52.4 grams of a
the theoretical quantity of ethylenediamine at
vary hard, light brown'wax were crystallized out.
an elevated temperature to form a fatty acid
This saturated fatty acid wax was found to be 50 amide; dissolving the mixture resulting from said
' only slightly soluble in warm methanol, and quite
i reaction in a heated solvent selected from the
soluble in warm benzol and xylol.
group consisting of methanol, carbonl tet
rachloride and hexane; cooling the solution-and '
- ‘_
Example IV
removing the precipitated amide.
A mixed fatty and rosin acid with a fatty acid 55
2. A process for separating the fatty acid~ and
-~ content of 83.3% lfatty'acid, had previously been
rosin acid components of acids derived from the
hydrogenated to prepare a mixture of` stearic
hydrolysis of kraft pulp mill soap which comprises
and rosin acids. 60 grams of this mixed acidV
the steps of: .reacting the mixed acids with the
were heated~ and mixed with 5.4 grams of ethylene
theoretical quantity of ethylene diamine at a
diaminelat a temperature of about 200°-210° C.~
for a period of 5j_h<_iurs.- The product was dis co temperature from about 150° C. to 225° C. to form
a fatty acid amide; 'dissolving the mixture re
sulting from said reaction in a 'heated ‘solvent
solved in a hot'aro'matic solvent followed by cool
ing, and 58~ grams of a hard, gray-brown wax were
crystallized- out. ~ - Melting
of \ crude
' In order- toxseparate thestearic acid wax com-`
pound from- theunreacted rosin acids, the crude
wax was _dissolvedÍin 200 cc. of hot xylol. On
selected from the group consisting of methanol,
carbon tetrachloride .and hexane; cooling the
solution and removing the precipitated amide.
. ¿M
JAMES r'. Locom
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