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2,412,5s1 ;
; Patented Dec. 17, 1946 ‘
- UNITED
STATE s
1 PATENT! OFFICE
'
2,412,561
' CONCENTRATION or FAT-SOLUBLE
~.
.
VITAMINS
.
Loran Old Buxton, East Orange, N. 1., asslgnor to I
National Oil Products Company, Harrison, N. 1., ..
a corporation of New Jersey
- No Drawing. Application August 4, 1942, .
Serial No.453,560
“X
lv
10 Claims.
.
' (Cl. 167-81)
.2
.
‘be indicated in the claims.
'duction of fat-soluble vitamin concentrates and ‘
a duced at the present time by many different
processes, the basic principle of the most com
mon commercial procedures involving the com
plete saponiilcation of the saponi?able matter in‘
a fat-soluble vitamin containing oil and the re
covery of the unsaponi?ablematter from the re
suiting soaps. Many attempts have been made
.
The first basic-step of the process invoives‘tlie ‘j '
in particular to a process of producing highly‘
1 potent concentrates of vitamin 'A.
Fat-soluble vitamin concentrates are being-pro
,
after disclosed, and the scopeof the invention will
This invention relates in generalto the pro;
.
‘ = *
extraction of‘ the original oil with a particular .
class of solvents hereinafter described. The sol;
vent employed in accordance with the process of
is
the invention may be selected from a large num-»
ber of aliphatic solvents‘found to be useful as a
result of extensive ‘experimentatiom' the choice _
10 of the solvent will depend to some extent upon .
the properties of the oil{ to be treated. as will '
‘become more evident vfrom'therletailed descrip
' "tion hereinafter given. Results have indicated
that the solventspreferably employed are mem- ‘. .
and proposals offered to improve the foregoing
saponi?cation processes with a view toward in
creasing the potency of the ultimate concentrate. 15 bers of well recognized chemical classes; it has.
also been found that the-number of carbon atoms
One such process involves the extraction of the ‘
in the solvent to be used is. a particularly im- ,
original oil with ethanol at room temperature and
portant' factor in determining the availability
the subsequent saponi?cation of the ethanol ex
tracted fraction. The latter process and many
thereof for use in the practice ,of this invention. -~
i I
others which have been proposed, including high 20 The following table sets forth the classes of-sol- ‘
V vents which have been found to be particularly
vacuum distillation, have fallen short in pro
viding highly potent‘ concentrates of vitamin A. '
It is the object of this invention tov provide. an
improved process for producing concentrates of
fat-soluble vitamins.
.
useful in the practice of this invention:
'
'
Table I
25,
Another object of the invention is to provide
an improved process for producing concentrates
of vitamin A.
'
'
Another object of the invention is to provide ,
l. Aliphatic and alicyclic monohydroxy alcohols ‘Q
. containing from 3 to 6 carbon atoms.-
,
2. Esters formed by the reaction of aliphatic and
alicyciic alcohols with aliphatic monocar
boxyllc acids, said esters containing not more ~ I
than. 8 carbon atoms.
highly potent concentrates of vitamin A.
so
3. Aliphatic ‘and’ aiicyclic aldehydes containing ‘
Other objects of the invention will in part be
obvious’ and will in part appear hereinafter.
.
I have discovered that the above and other
objects of the invention may be realized by ex
tracting a fat-soluble vitamin-containing marine ‘
oil with a solvent which is characterized by be
not more than 6 carbon atoms.
.
7 4. Aliphatic ketones containing not mor
carbon.
atoms.
_
.
’
than 8
.
‘
>
Solvents falling in the classes above listed are ‘
all liquid aliphatic organic compounds charac- '
ing miscible with the oil at temperatures above
terized by being miscible with fat-soluble vitamin
room temperature and partially immiscib e there
with at temperatures below room tem erature.
contalnlng marine oils at temperatures above
saponifying the solvent-extracted fraction and
recovering the unsaponi?ed matteryfrom the re
sulting soaps. Preferably-several extractions of
tially immiscible therewith at temperatures be
.- the fat-soluble vitamin-containing marine ‘oil are,
room temperature, 1. e.”20° to 25° C., and par- j
low room temperature, and it has‘ been found that
’ solvents falling within these classes of compounds
may be ‘used in the practice of this: invention.
carried out and the resulting extracted fractions
each saponifled separately or any two or‘more
of these fractions combined and then saponiiled.
In any case the resulting unsaponi?able matter
In order to more'full'y illustrate the nature of
the solvents which may be- employed, a partial
obtained from any fraction or combination there
of will have a higher vitamin A potency than the
. list thereof is given herewith; it is to be under; ‘
. stood, however, that thislistis not intended to '
unsaponi?able matter produced directly from the
be complete, but is merely illustrative of the sol
vents which may be employed. Thus it has been
original oil by saponi?cation alone.
_»
The invention accordingly comprises the sev
In addition it will be noted that the preferred sol-. , ‘
vents possess relatively‘ low freezing points.
found that the following solvents may be used: - _
n-propyl alcohol, isopropyl ‘alcohol, isopropyl- ,
amine. n-butyl' alcohol, n-amyl alcohol, isoamyl 7
steps with respect to each of the others thereof,
which will be exemplified in the method herein 55 alcohol. secondary amyl alcohoLfurfuryl alcohol. .
eral steps and the relation of one or more of such
, 2,419,581
~
3
vitamin A at temperatures above this value. It
is preferred to form the solution of oil in the sol
vent by ?rst heating the solvent to be used to
allyl alcohol. diacetone alcohol, e-hydroxy ethyl
acetate, methyl formate, ethyl formate, ethyl
acetate. methyl acetate, isopropyl acetate. glycol
diformate. glycol diacetate, methyl levulinate,
a predetermined temperature at which the oil
to be added'will substantially completely dissolve
ethyl levulinate. methyl aceto acetate, ethyl aceto
in ‘the solvent, and‘then adding‘the ‘oil to the sol-rv
vent with ‘agitation-the operatio'nebeing carriedv
out ,inan ‘inert gas atmosphere.
acetate. methyl furoate}, vinyl“ acetate, fur- >
fural pronionaldehyde, crotonaldehyde, acetone,
methyl ethyl ketone, acetonyl acetone and pro
The ‘solution of the vitamin-containing oil in
pylene chlorhydrin. Mixtures of .these solvents, 10 ‘the i solvent prepared ._ as . hereinabove described
‘may also be used. It will be noted that all these-I‘
may ‘then, in accordance with the process of the
solvents belong to that class of aliphatic organic
invention, be permitted’ to cool so as to e?'ect a
compounds which has the property of, being mis- ,, . separation of the solution of the highly potent
cible with fat-soluble vitamin-containing marine __
vitaminextr'actfrom' the remainder 'of the oil.
oils at temperatures above room temperature
The temperature to which the solution is cooled
and partially immiscible therewith at temperae
-' may'vary from about room temperature to as
tures below room’ temperature; furthermore, it ' i 1 low as’-‘-'70° C.‘ or lower. It has been found, how
will be noted that the majority of these solvents ’
it ,iSpre?etable to cool the solution with
weather
agitation to temperatures somewhat below about
have relatively low freezing points.
Occasionally it may be found'that certain of I
0°C., e. g. in the neighborhood of —18° C. Upon '
the solvents'hereinabove mentioned may be-too 20. .cooling, the solution‘ separates into two layers,
miscible with some of the oils]v which may beq' ' I‘ one layer composed‘ chie?y ‘of the portion of .the
treated by this invention :to: effect .a separation;
original oil insoluble vin the solvent at‘low tem-
of highly potent: vita-min fractions therefrom;
T peratures and
the other ' layer composed of the
‘.1
'
thus, for examnlaacetone is toomiscible with ; .
solvent solution, of a highlyv potentvitamin frac
some fat-soluble vitamin-containing oil to ace,v 25v
7 compllsh the purposes'ofzthisinvention. ,-HoW.-. . - ‘tion.
‘ The solvent
’ layer
;' 1_~_obtained upon . coolingthe
ever. this condition can bev easilyacorrectedby ‘solution may be filtered and'then treated to re
diluting the solvent either with a smallarnount
"movethe' ‘soIvent-thereIrOm-Le. g. by vacuum (115- :»
of water‘orwith'a liquid aliphatic'rorganic-‘sol-I
vent relatively. immiscible with fatty oils.’ In; gen- ,
tillation, whereby-an oil ‘is recovered having a
50
eral it may be said that the effect of diluting-any
vitamin potency far inexce'ss'of that of the orig
' ' inal oil;,the‘pe'rcent'age increase. in vitamin po- ' ~
of the above solvents with water will be to-render ‘ "‘tency may be anywhere between ‘about 50 %; and
the solvents more ‘immiscible-‘with fatty oils, so = ‘ about 400%., If desired, the solvent extraction, "
that if difficulty is encountered in effecting-Proper V
may‘be carried’ out. by-continuously contacting ,~
separation ofrthe highly potent extracts fromthe .35 'a'body of- a fat-soluble vitamin-containing-oil‘
vitamin-containing oils, this. di?lcultycangen- .7 [,with one of the above solvents at-a relatively low
erally be overcome 'by the addition of a small ‘f’ ‘temperature, e.» g. around --18° 0;; this method ~
a‘ continuous extraction‘ of
amount of waterte the solvent. ‘ ,
_
The solvents preferably employed. intheprac- 1' "of. operation- eifects'
cases at least 2 ‘extractions ofthe
theoil.
fat-,.
tice of theinventionare the aliphatic'l'valcoholsr 40 _ 'f a highly potentjvitaminfraction'froin
In most
‘soluble vitamin-containing‘oil should be made, ,
containing from 3'to 6. carbon atoms: of these I
solvents isopropanol and diacetone alcohol have
and 3 to 6 more" extractions are preferably made. 1
proved to be the most successful. The presence ' The first extractwhich is obtained is preferably
of the hydroxyl group seems to impart to these:
vsa'pom'i‘led and the vitamins recovered‘therefrom .
solvents properties which make them particularly 451 V_ vseparately from the other extracts. The; second ' 7.
useful for the present purposes; whether this fac
and subsequent extracts may either-‘be combined .7
tor is duej'to' some activating in?uence possessed‘, . and then saponi?ed and the vitamin concentrate
by this group is not known, but it is believed that .
recovered therefrom or each extract may be
the presence ofthe hydroxyli‘group in such.sol
saponi?ed separately and the unsaponi?able
vents makes them more capable' of'extracting‘ 50 matter then recovered vfrom ‘each saponi?ed ex-v '
vitaminA esters from oilsicontainin'g ._ such esters.v ; tract. I have found'th'at invariably. the ?rstex
In carrying’ out the process of the invention the
tract contains the lowest ratio of vitamins inre- ,
fat-soluble vitamin-containing marine oil tobe
lation to the totalunsaponi?able matter when I,
treatedis ?rst mixed with any particular solvent
' compared to. the 'subsequentextracts of the same 1
of the aforementioned type. The oil treated may ‘i
'
be any of the marine oils containing. vitaminA
voil.
'
'
'
:In many cases the increases
ratio of vitamin).
successivelytothe
from
with orwithout vitamin D, such as, for'exa'mpla' ' 1 unsaponi?able matter
cod liver :oil, shark liver oil, tuna liver oil, hall? ' the ?rst to the sixth‘fra‘ction extracted from a
but liver oil,;mackerel»liver_ oil,.ling cod liver'oil,
sole liver‘oil, spear; ?shliver oil, sword ?sh liver
,
.
given oil. In‘ view thereof, it is preferable, par
60
ticularly when exceedingly high potent vitamin A
oil, sardine. oil, herringyoil, menhaden‘oil, whale _ ‘ concentrates are desired, to saponify each frac- ; I
'liver oil, etc.‘ The relative proportion'of oil to
tion separately. In most cases, however, all of v
solvent in the mixture may varywidely'; prefer ‘ a the fractions from the vseconclon may be-com- _
ably'the ratio of. solvent tooilrshould be greater
bined priorto saponi?cation as the ?rst extract
than-one andin most cases mixtures containing," 65 appears ‘to'contain a much‘ higher ratio of un-. I,
between about 2% and,about 25% oil are'm'ostv ‘i
' saponi?able matter to vitamlnA than each of the _ .
suitable. ‘Thismixture maythenbe heated until I ,
the oil orthegreater part thereof is dissolved in
the solvent.w The temperature. to which the mix
ture of oil an solvent is heated-may vary widely‘
contained. in .the mixture; in general it maybe
‘
having a higher potency than a‘ concentrate pre
pared by. directly saponifying'the same 011.; It is
to obtain
possible by the‘ processof the invention
}
"vitamin A concentratesvon'h commercial scale
having a potency of ‘above 3,000,000 units per
75 isram, i; e. essentially pure vitamin-A; Inprder
' stated that ‘it is inadvisable to heat fat-soluble
vitamin-containing‘oils to temperatures-inexcess '
of 175° c. because of the relative instability of
succeeding fractions. in any event, however. the ‘
?rstrfractio'n-will yield a_vitamin A concentrate y y ,
70
depending upon the nature of the ingredients 7
_
.
9,419,561- I
the mixture warmed to about '33’ C. to dissolve
the oil. The solution was then cooled gradually to
about —25° C. and after about 24 hours the upper
to determine whether or not to saponify the ?rst
and subesequent extracts separately or together,
it is usually advisable to run laboratory tests on -
isopropanol layer was decanted and ?ltered. The _
small samples of each extract to determine the
ultimate potencies to be expected.
insoluble. solidi?ed oil layer was re-extracted
a
three ‘more times as above. Each isopropanol'
extract fraction was freed of isopropanol sepa
The saponi?cation of the extracts and the re
covery of the unsaponi?able material therefrom
may be carried out in any suitable manner. In f
all cases, it is preferred, of course, that the ex; .
rately. by subjecting the same to distillation under
reduced pressure in the" presence of N2 gas‘. The
‘tracts be recovered from the polar solvent solu 10. following unsaponi?able and vitamin A"‘values 3
tions thereof before they are saponi?ed.
on the crude oil and on the four separate iso-‘
Prefer- '
ably the saponi?cation of the extracts is carried
out by the process of application, Serial- No.
propanol extract fractionsv bring out clearly why
333,114 of Buxton and Simons ?led May 3, 1940,
ond, third and fourth extract fractions-are'ma
terially more potent in vitamin A than similarly
‘prepared fractions from the crude oil'or fro the
unsaponifiable fractions prepared frorn'theisec?
which has issued as Patent No. 2,318,748, or the
process of application, Serial No. 350,166 of Bux- ‘
?rst isopropanol extract fraction.
ton and Colman, ?led August 2, 1940, which has
issued as Patent No. 2,318,749, since much more efficient recovery of the fat-soluble vitamins'will
- I
Unsaponi-
'
?ed value
be
obtained.
.
.
.
.
‘
mm A per
-
For a fuller understanding of the nature and
objects of the invention,'reference should be had
to the following examples which are given merely
.
Crude oil .... ..' ..................... ..
5. 4
First isopropanol extract ............ ..
Second isopropanol extract..
.
.13. 0
’ 11.0
to further'illustrate the invention and are not to
Third isopropanol extract. ...-
be construed in a limiting sense all parts given_ -
Fourth isopropanol extract .......... ..
» '
8.8
8. 4
being by weight and all vitamin potencies being
expressed in‘U. S. P. units.
,
.
Example I
100 parts of crude shark liver 011 containing
99,000 U. S. P. units of vitamin A per gram were
mixed with 400 parts of 99% isopropanol and the
mixture warmed to about 35° C. to dissolve the oil.
The solution was then cooled gradually to about
—25° C. After about 48 hours the upper iso
propanol layer was decanted and ?ltered. The
insoluble solidi?ed oil fraction was re-extracted .
three more times as above.- The four isopropanol
extracts were combined, ?ltered and the iso
propanol removed by distillation under reduced
pressure and in the presence of N2 gas.
100 parts of the combined isopropanol extracts
containing 262,000 U. S. P. units of vitamin A per
gram were mixed with 50 parts of ethylene di
20 parts of, each ofvthe above samples were 7 ’
completely saponi?ed and the unsaponi?able
fraction recovered'as described'in Examplel'.
The following vitamin Aresults wereobt'ainedon
the unsaponiflable' fractions. fromeachxsdpfjqthe
- aforesaid samples.
. I‘
1
A
_
._ g
,
Crude oil" i
'
1,509,000
First isopropanol extract___‘__;_____‘_
" Second isopropanolextract ____ .._-____
. 1,570,000
2,03%900- ‘ ‘
Third isopropanol extract__________ ___v2_,4_70,_000
‘ Fourth isopropanol extract ______ ______'_ 2,050,000
It is evident from the above description are-- ~
examples that the process of the invention pro-q ‘
vides a highly efficient "means for utilizing a fat
chloride and 3 parts of 99%‘ isopropanol. While
soluble yitamin-containing marine oil to the best
advantage; Highly potent concentrates of ‘fat; '
stirring in the presence 0f.N2 ‘gas su?icient 45%
aqueous KOH (43 grams) to completely saponify
are in fact much more potent than those obtained‘
- the oil was added.
After about 20 minutes the
,
“Units
on the
vitamin
unsaponi?able
A per gram -'
soluble‘vitamins are obtained, concentrates which
by the usual concentration processes‘; and in ad
dition, a large percentage of the vitamin-contain
stirring was ceased and the resulting thick super
solvented emulsion insulated and allowed to stand 60 ing oil is left in its original form and not de
stroyed as withthe usual processes. This resid
at room temperature over-night. The soap-mass
ual oil usually contains a certain amount of fat
was then heated to about 60° C. while stirring in
soluble vitamins and may be advantageously'jem
the presence of N2 gas for about 30 minutes to
‘ break the emulsion and to ?occulatethe soap.
400 parts of ethylene dichloride and sufficient wa~
ter to bring the moisture content .of the soap up
to about 24% were added and the soap-mass
cooled to room temperature. The stirring was
stopped and after about 30 minutes the lower
solvent layer removed. The ?occulated soap par
' ticles were then extracted six more times with 400
part portions of ethylene dichloride. The seven
ethylene dichloride extracts were combined, ?l
tered and the ethylene dichloride removed by dis
tillation. The ‘recovered vitamin A alcohol con
centrate contained 2,400,000 U; S. P. units of vita
min A per gram. A concentrate produced di
rectly from the crudeoil by the above saponi?ca
tion process yielded a. product containing 1,600,
000 U. S. P. units of vitamin A per gram.
.
ployed to supply the vitamin needs of livestockv '
and poultry by admixing the oil" with livestock
and poultry feeds in, the usual manner._ In case
the vitamin potency of this oil is slightly below
' that desired for use in farm feeds, it may; easily -,
. be adjusted to the desired potency with concen-l -.
trates of the necessary vitamin.
Since certain changes may be made in carrying‘ I
out the process without departing from the' scope
of the invention, it is intendedy‘vthat all matter‘ v_ "
contained in the above description shall be in- _
terpreted as illustrative and norm alimiting
sense.
.
>
'
'
‘
Having described my invention, what 'Iclainii
as new and desireto 'secureby-LettersPatent is;
'1. A process of producing an‘ improved'fat- ‘ h
soluble vitamin concentrate, ‘which comprises '
contacting a fat-soluble vitamin-containing ma
> rine oil with a solvent selected from the group
' 100 parts of crude shark liver oil containing
106,000 U. s. P. units of vitamin A per gram were
consisting of aliphatic and alicyclic monohydroxy
alcohols containing from 3 to 6 carbon atoms,,
mixed with 4000 parts of 99% isopropanol and 75 esters formed by the reacton of aliphatic and all
8,418,581
7
8
'cyclio alcohols with aliphatic monocarboxylic
bon atoms, aliphatic and alicyclic aldehydes con
acids, said esters containing not more than 8
carbon atoms, aliphatic and alicyclic aldehydes
taining not more than 8 carbon atoms and all
phatic ketones containing not more than 6 carbon
,atoms, heating the mass to dissolve at least a
containing not more than 6 carbon atoms and
major portion of the oil in the solvent, cooling
aliphatic ketones containing not more than 6
carbon atoms, heating the mass to dissolve at
least a major portion of the oil in the solvent,
cooling the mass to a temperature within the
range of 0° C. to —-70° C. whereby layers are
donned. separating the solvent-soluble fraction
from the mass, saponifying said soluble fraction
and recovering the unsaponi?ed matter there
the mass to a temperature within the range of
0° C. to --70° C. whereby layers are formed, sep
7 arating the solvent-soluble fraction from the
mass, re-extracting at least twice more the sol
m
' from.
vent-insoluble fraction as above, saponifying said
soluble'fractio'ns and recovering the unsaponii'led
matter therefrom.
'
7. A process of producing an improved fat
soluble vitamin concentrate, which comprises
2. A process of producing an improved fat
soluble vitamin'concentrate, which comprises con 15 contacting a fat-soluble vitamin-containing ma
rine oil with a solvent selected from the group
tacting a fat-soluble vitamin-containing marine
oil with a solvent selected vfrom the group con
' consisting of aliphatic and alicyclic monohydroxy
alcohols containing from 3 to 6 carbon atoms,
heating the mass to dissolve at least a major por
cohols containing from 3 to 6 carbon atoms, heat
ing the mass to dissolve at least a major portion 20 tion of the oil in the solution, cooling the mass 4
to a temperature within the range of 0° Cato
of the oil in the solution, cooling the mass to a
-70° C. whereby layers are formed, separating
temperature within the range of 0° C. to —70° C.
sisting of aliphatic and alicylic'monohydroxy al
' whereby layers are formed, separating the sol
the solvent-soluble fraction from the mass, re
extracting at least twice more the solvent-insol
vent-soluble fraction from the mass, saponifying
said soluble fraction and recovering the unsa 25 uble fraction asabove, saponifying said soluble
fractions and recovering the unsaponiiled matter
ponifled matter therefrom.
therefrom.
3. A process of producing an improved fat
8. A process of producing an improved fat
soiuble vitamin concentrate, which comprises
soluble vitamin concentrate, which comprises
contacting a fat-‘soluble vitamin-containing ma
rine oil with isopropanol, heating the mixture to. 30 contacting a fat-soluble vitamin-containing ma- '
rine oil with isopropanol, heating the mixture
dissolve at least a major portion of the oil in the
to dissolve at least a major portion of the oil in
isopropanol, cooling the mass to a temperature
the isopropanol, cooling the mass to a tempera
within the range of 0° C. to —'l0° 0. whereby lay
ture within the range of 0° C. to —70' C. whereby
ers are formed, separating the isopropanol-s'oiu
blo fraction from the mass, saponifying said sol 35 layers are formed, separating the isopropanol
soluble fraction from the mass, re-extracting at
uble fraction'and recovering‘ the unsaponiiled
least twice more the isopropanol-insoluble frac
matter therefrom.
tion as above, saponifying said soluble fractions
4. A process of producing an improved fat-sol- .
and recovering the unsaponiiied matter there
ubie vitamin concentrate, which comprises con
from.
tacting a fat-soluble vitamin-containing marine
9. A process of producing an improved fat
oil with diacetone alcohol, heating the mixture
soluble vitamin concentrate, which comprises
to dissolve at least a major portion of the oil in
contacting a fat-soluble vitamin-containing ma
the diacetone alcohol, cooling the mass to a tem
rine oil with diacetone alcohol, heating the mix
> perature within the range of 0° C. to -*70° C.
ture to dissolve at least a major portion of the
whereby layers are formed, separating the diace
oil in the diacetone alcohol, cooling the mass to
tone alcohol-soluble fraction from the mass, sa
ponify‘ing said soluble fraction and recovering the ' a temperature within the range of 0° C. to —70°
C. whereby layers are formed, separating the di
unsaponi?ed matter therefrom.
.
.
,
5. A process of producing an improved fat-sol- .;
uble vitamin concentrate, which comprises con
tacting a'iat-soluble vitamin-containing marine
oil with aqueous acetone, heating the mixture to
dissolve at least a major portion of the oil in the
aqueous acetone, cooling the mass to a temper- '
ature within the range of 0° C. to —70° C. where
by layers are formed, separating the aqueous ace
acetone alcohol-soluble fraction from the mass,
re-extracting at least twice more the diacetone
alcohol-insoluble fraction as above, saponifying
said soluble fractions and recovering the un
saponiiied matter therefrom.
10. A process’ of producing an improved fat
soluble vitamin concentrate, which comprises
contacting a fat-soluble vitamin-containing ma
rine oil with aqueous acetone, heating the mix
ture to dissolve at least a major portion of the
poni?ed matter therefrom.
'
oil in the aqueous acetone, cooling the mass to a
60
6. A process of producing an‘improved fat
temperature within the range of 0° C. to —70° C.
whereby layers are formed, separating the aque
soluble vitamin concentrate, which comprises
contacting a fat-soluble vitamin-containing
ous acetone-soluble fraction from the mass, re
extracting at least twice more the ‘aqueous ace
marine oil with a solvent selected from the group
consisting of aliphatic and alicyclic monohydroxy
tone-insoluble fraction as above, saponifying said
tone-soluble fraction from the mass, saponifying
said soluble fraction and recovering the unsa~
alcohols containing from 3 to 6 carbon atoms,
esters formed by the reaction of aliphatic and
alicyclic alcohols with aliphatic monocarboxylic
' acids, said esters containing not more than 8 car
soluble fractions and recovering the unsaponi?ed
matter therefrom.‘
LORAN OID BUXTON.
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