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Патент USA US2404365

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preteens- 23, 1946' I.
_ 12.404.365
uulreo "sTA-TEs2,404,365Partial" ' {OFF-ICE 1 1
ss'raa concanraa'ras
i'ciliarles E. Dryden, East 0range,_and Loren-0;"
Boston, Newark, ‘N. 1., assignors to National
Oil Products Company. Harrison, .N. 1., a cor
poraticn'ot New Jersey
Application September 28, 19:44, I
‘Serial No. 556,284 -
The present'invention relates to the produc-'
tion of fat soluble vitamin concentrates from
natural oils and fats containing the same. More
drolyze only a- minor proportion 01 the vitamin
A ester'in the original oil to the vitamin alcoq
hol. By proceeding in this manner, it is there-.
possible to produce ester concentrates of
partlcularlypthe present invention relates to the 5 iore
considerably greater potency than the ‘original
production of relatively high potency vitamin A
concentrates wherein the vitamin'A is largely
in natural ester form from materials of marine‘ '
origin containing vitamins A and D.
011 while at the same time hydrolyzing _ only a
small amount of the ester of the original oil.
Although it has been proposed in accordance
with the aforementioned application tor-reduce the
Various methods of concentrating the 'vita
min content of oils of marine origin containing 10 speed of reaction as ‘by limiting the amount of _
catalyst or the concentration of the alkali and"
_ vitamins are known in the art, amongthem, proc
although the slower reaction thus e?ected has in
esses which inc ude saponi?catio'n or the fatty
creased the potency oi the vitamin A ester pro
acid glycerides by means of caustic soda or caus
tic potash. In general, prior art saponi?catlon ' duced, ithas not been possiblewhen proceeding
processes contemplate complete saponiiication of 15 with the reaction under adiabatic conditions,v as
all ‘the saponi?able constituentslot- the oil in an
' effort to produce concentrates of vitamins of the
highest potency. In a- process of this character,
- the vitamin and other'higher alcohol esters are
set forth in the prior application, to slow down
the speed or reaction su?lciently to greatly in- _
‘crease the potency of the ‘resultant vitamin ester
concentrates by such means. Inasmuch as the
converted to soaps; vitamin alcohols and other 20 reaction with the alkali is exothermic, the. tem-'
perature of the mixture of alkali and the oil being
higher alcohols. Vitamin alcohols are separated
treated normally rose to a ‘temperature of ap
- from the residual soaps and other components of
e concentrate thus produced is of a _ proximately 50-60° during the reaction,'and this
the oils; _,
was true no matter'how slowly the caustic was
relatively/high potency, but the vitamin is sub
stantially completely ‘in ‘an ‘alcohol form rather 25 added during saponi?cation. In accordance with
the teachings of the prior art, this was not undes
than in the natural ester form. Among the dis
sirable, since some of the prior patents even taught
' advantages of such a, process is that the vitamin
v _
alcohol is much more subject to oxidation and
upon storage for any length of time exhibits a
the desirability of heating the mixture of caustic .
and oil in order-to produce a more-complete .sa
to' partially saponify the saponi?able matter in
and at- the .same time a lesser amount of vita
ethylene dichloride and the resultant nonsaponis
clearly understood, but it is ‘evident that that
portion of the fatty‘ acid glycerides'which- is not
lesser biological potency than the natural ester. 3° poni?cation.
In accordance with the present invention, how
In 0‘. S. application Serial No.'450,'757, a-process
ever, it has now been dis vered that ii the re
involving a partial saponi?cation of fish liver
\ action mixture-o1’ causti and oil is cooled during
oils and the like to produce vitamin concentrates
the reaction so that it, is maintained under iso
wherein a substantialportlon oi the ‘original vita
min content is obtained in ester form is disclosed. 35 thermal conditions and preferably at tempera- .
tures below approximately 35° C., a much higher
The process set forth in the aforementioned ap
plication includes the addition of sufficient alkali . potency vitamin ester concentrate is ‘produced
min A ester‘ is hydrolyzed to vitamin A alcohol.
the oil. ‘Thereafter the soap formed is separated
as by extracting the nonsaponi?ed residue with 40 The exact reason for this phenomenon is not
' - lied residue after removal of the ethylene ‘dichlo
ride is then further extracted with a polar sol
vent such as methanol to remove the‘ vitamin
A alcohol. ‘The resultant ester-concentrate pro-‘
duced is of considerably higher potency than the
original oil. However, there are limits to the
strength of the'ester concentrate produced from
saponiiled during the incomplete saponi?cation .
is rendered soluble in a polar solventsuch as
methanol, probably
Thus when
due the
to mono
after separa- .
tion of the'soap .istreated with a polar solvent
such as methanol, a relatively largeproport'ion ‘of
any particular oil since a higher degreeof sa- '
the nonsaponi?ed nonvitamin content is removed
poni?cation tends to hydrolyze a greater ‘amount
of the vitamin ester to the vitamin A alcohol. In;
practicing the process '0! the aforementioned'ap
to leave behind a more potent vitamin ester con
plication; therefore, ‘the vitamin-containing oil;
is saponi?ed to an extent which will produce-the
centrate. ' Further, during the reaction a much
lesser quantity of the vitamin ester is hydrolyzed
to vitamin alcohol. It has therefore become pos-,
sible to not only separate the vitamin ester in
highest potency esterrconcentrate and still hy I55 relatively large yields from the remaining com
ponents of the oil, but also to concentrate the '
ester by means of a simple process ‘so thatyvita
poniflcation, a- substantial proportion of the'vita
min esters remains intact, and the ‘saturated glyc
erides are substantially‘ completely saponiiicd
min ester concentrates of relatively high potency
are produced.
prior application, under conditionsof partial sa
Further, higher yields are ob
tained considering, both, vitamin esterv and alco
hol as compared to the ‘total amount of vitamin
along with a portion cf-the unsaturated glycerides.
in the ‘original oil.
process, i. e. the low temperature and isothermal
saponi?cation, a much lower percentage of vita~
In general, when proceeding with the present
'. It is one of the objects of the present invention,
, therefore, to prepare vitamin concentrates ‘from
~ min alcohols is produced than when proceeding in ,
natural vitamin containing materialsby partial.
accordance ‘with the process of the prior applica
saponi?cation, while cooling the oil so as to pro
tion. ‘ Av certain amount of vitamin'alcohols, how-'
duce vitamin ester concentrates of relatively high '
ever, naturally occurs-in the oil, and the unsa
poni?ed mass contains this small proportion of
. vitamin alcohol, a part of the unsaturated glyc-r
A second object of the- present invention fisto
provide an'isothermic process for the partial sa 15 erides present in the original oil un'saponi?able ,
poni?cation of ?sh liver oils and the'like,-,whereby . - matter, glycerine, soaps, etc.
. _
a much lesser proportion of. vitamin ester is hyé .
‘drolyzed to vitamin alcohol.
The present process vcan be practiced, at least to
some degree, with any degree of saponi?cation of
A third object of the present invention is
the oil up to approximately 98% saponi?cation.
partially saponify a vitamin ester containing ma 20 In general, the amount of the caustic em'ploy‘ed
rine' material while cooling the same so as to form‘
will be that equivalent to somewhat less; than
as large a, proportion as possible of polar solvent
98%, with the larger amounts of caustic increas
soluble material from the unsaponi?ed non-.
ing the potency of the vitamin alcohol portion vitamin components so that upon treatment with
extracted by means 'of' methanol and correspond
a polar solvent such as methanol a vitamin ester 23 ingly tending to hydrolyze a greater p'roportiornof
concentrate of a relatively high potency'remains. '
the vitamin ester to the alcohol. In general, 'suiii
cient caustic will be employed in the presentprocj
ess equivalent to the saponi?cation of from 60
Other objects and advantages cf‘. the present
invention will be apparent from the present de
scription'_ and claims.‘
to about 95 %_ of the saponi?abie matter in the oil.
In general,‘ it is preferable when practicing the at The saponi?cation reaction may be retarded by
present process _to add the caustic at a relatively
slow‘rate. Thus aportion'of vthe caustic may be
added in relatively concentrated form over a sub
other means in addition to the temperature con->
trol, for example, the oil may bediluted with a
suitable inert solvent such as a ‘nonpolar solvent
on the order of ethylene dichloride, vheptane, tri
stantial period, and the additional caustic added
in relatively dilute form over another period;
. ohlorethylene, hexane, cyclohexarie, methyl cyclo
or, in the ‘alternative, a relatively more dilute ,
hexane, or a mixture of inert solvents. If a solv
caustic'may be‘slo‘wly added. In general, " the
ent is employed-the weight of the solvent should
range from about 15 to 99% and preferably from
lower the temperature ofreaction, the less the
quantityofv ester converted to alcohol form, “and '
about 25-75% to obtain the most e?icient selective ,
the temperature of reaction should be as low as
_ saponiflcation.
possible depending on the temperature at which‘
the oil tends to solidify and the reaction tends to
narily employed in the saponification reaction.
Usually, in saponi?cations of this type‘, from- about
"slow up to such an‘ extent that a c‘omplete'reac- .
tion will not take place. In general, temperatures
' ‘2 to 5% of isopropanol or other polar catalyst is'.
' below about 35° 0., are used and temperatures
employed. .This allows the saponi?cat'ion reac
- from 0° C. to 25° C. have been found to be par
tion to take place without high heating. v How-v
ticularly wsuitable. ‘As may be understood, the
ever, fromv 1/2 to'l% of isopropanol or other cata-'
temperature of the reacting ‘mass may be kept at '
lyst has been found satisfactory, even at the low
the desired range during saponi?cation byany
suitable cooling means.
may. also be re
tarded ‘by reducing the amount of catalyst ordi- _
temperatures of the present process. ' .The speed '
The'preseht process is applicableto the pro
of the reaction may also be retarded by utilizing
"less concentrated caustic.
duction ~of vitamin concentrates from various
It will be understood from the foregoing that
types‘ of vitamin containing materials and par- , I the present reaction may be retarded in order to
* ticularly materials of marine origin containing >
produce the greatest potency ester concentrates‘
. vitamins A and D. Such oils are the ?sh liver oils 55 'by'the use of a solvent'or diluent of an inert
such. as cod liver oil, ling cod liver ‘oil, pollack .'
liver oil, tuna liver oil, shark liver oil, dog?sh
liver oil, mackerel liver oil, sword ?sh liver oil,
spear ,"?sh liver' oil, sole liver oil and halibut liver .
character, by use of a lower catalyst concentra
?t-ion and a lower caustic concentration.
‘In gen- _
eral a caustic concentration equivalent to 30% to
50% of caustic soda or potash is suitable. , All
oil. ‘Marine oils. such as sardine 'foil, pilchard'oil, .60. of these factors, however, do not give rise to the
‘herring oil, seal oil and whale oil are also suitable.
_' desirable results ofvthe present invention, unléss
In place of the oils which havebeen obtained
the. temperature is' also maintained at a rela
from the 'raw material by cold pressing processes
low level, as before stated, below'approxi
or other conventionalv means, solvent extracts
mately 35° C.
and partial concentrates of oils. of the character 65 After‘, the saponi?cation is completef i. e‘. in
described may also be used as, for example, the
isopropanol extracts of the liver and marine'oils
from 1 to 12'_hours, the semi-concentrate is ex
, tracted from the partially saponi?ed mass bythe _
use or a nonpolar solvent. The particular method
The partial selective'saponi?cation is carried . forthe extraction is described in ~detail in co
out ‘by treating a vitamin-containing material of 70 pending application Serial vNo. 533,256, wherein
the character set forth with caustic in the man
it is pointed out that the separation of the soap .
ner well known in the art for preparing vitaminj
from the solvent should preferably take place at
concentrates, except that the amount 'of caustic
an elevated temperature as, for example, ‘from
used- isa'lways insu?icient' to completely saponify
40-80°‘ and preferably from 60-70" C. Further,
the oil." "As‘pointed out in the aforementioned 75 during this separation which takes place rapidly
5 .
about % hour. The average temperature of the
at this elevated temperature, the amount. or
oil and soap mixture during'mixing was about
water present should be regulated from 12-35%
13° C. The soap produced was extracted suc
cessively withv 500 cc. of ethylene dichloride at
65°C., a total of six extractions being made. The
combined extracts were kept at 0° C. overnight,
/and, in some instances, as high as 50% as com
pared to the weight of the soap produced. Pref
erably, the amount oiwater should be deter
mined by the solubility of the soap in‘ the ex
?ltered and the solvent removed under vacuum.
traction solvent, preferably ethylene dichloride;
the amount or water being regulated so that from
1/g to 5% of the soap and preferably somewhat
The semi-concentrate thus produced had a po
tency of 331,000 units 01' vitamin A per gram.
The present low temperature saponi?cation gives
three times with 5 volumes of methyl alcohol, the
mixture of alcohol and semi-concentrate being
?rst heated to 50° C. and then cooled to —18° C.
. less than 1% is soluble in the ethylene dichloride. 10 Thereafter the semi-concentrate was extracted
~ rise to vitamin ester concentrates of the highest
potency when used in conjunction with the high
and decanted. The vitamin content of the residue ~
temperature rapid extraction of the semi-con
centrate from the soap produced in accordance 16 ester fraction was equivalent to 58% of the total
vitamin A' recovered. The potency of the ester .‘
with the just- mentioned prior application.
fraction was v477,000 unitsof vitamin A per gram.
It is to be noted that although in this prior ap
The total overall vitamih A recovery, i. e. the
vitamin A in the methanol extract as well as that
- plication it is pointed out that-it is desirable for
the extracted vitamin semi-concentrate to remain
in contact with alkali for the shortest period of 20 in the residue was equal to 97.9% of the original
vitamin A in the oil. A‘ similar reaction to the
time so that the biological potency of the "con
above was carried out, except thatthe oil was not
centrates produced may be enhanced, even though
cooled‘ during saponi?cation. The temperature
in the present process the low temperature sa
in this case rose. to a maximum of 62° C. in 7
poni?cation takes a considerable length of time
as compared to relatively‘ high temperature'sa 2.5 minutes. As compared to the reaction- at low
temperature, only 38.9% vitamin A was recovered
poni?cation, this does not have a deleterious ef
in ester form. Although the semi-concentrate
feet on the concentrates produced. ‘This is prob
- produced had a potency of 300,000 units or vita
ably due to the low temperature involved. How
min A per gram, the potency of the ester frac
ever, after the saponi?cation reaction is complete
and the mass oi’ soap and saponiiied matter is 30 tion i. e'..the methyl extract residue of the semi
concentrate was only 172,000 units of vitamin Av
heated, as' by the addition oi.’ hot solvent for
per gram. The overall yield of vitamin Alfrom
fractionation, it is desirable at these'tempera-'
the high temperature process was 943%,.
tures in the neighborhood of 50-80° C.that the
Example II
separation of‘ the soap‘ tromthe solvent extract
take place as rapidly as possible. The extraction 3.5.. lootgrams of soupfln" shark liver oil-‘having
may then be'carried out a number of times with _
lesser quantities of ethylene dichloride or other
suitable solvent'as' mentioned in the prior ap
pllcation. and the resultant concentrates com
bined. Thereafter,‘ the‘ ethylene dichloride is re
moved by any suitable-means to produce a semi
concentrate. The semieconcentrates may then be
1 103,000-unlts of vitamin A per gram were placed
in a beaker unmersed in ice water maintained at ,
a'temperature of>-3° C. with ice. 0.75%. by
40 weight of isopropanol was added and then sum- '
fractionated by means of polar solvents or they may
be fractionated by processes other than selective
' solvent extraction as, for example, high vacuum 45
- distillation, vacuum distillation, absorption, etc. It
is preferred, however. that a fractionation with _
~-polar solvents be carried out and preferably the
polar solvent used is methanol or ethanol. However,
cient 49% KQH to saponify 90%‘ of the glycerides in the 011, i. c. 33.4 grams of 49% KOH were 1
added dropwise while stirring. The KOH was .
' added'during a period of 1 hour and the mass“
was mixed .for an additional 1/2_ hour. ‘There
after, sufficient water ‘was added to bring the
moisture content of the soapforined, on a wet'v
basis,“ to 23.5%. The average. temperature of
the'oil during saponi?cation was'3" C. and after -
' a
mixing‘ and'addition of water, the mass was Y. ‘
any other solvent which is characterized by being 50 ‘stored
at 3° C. for 42 hours. Thereafter the-soap . '
miscible with (a solvent for), ~vitamin alcohols I was extracted
?ve times with ethylene dichloride
but immiscible with (a nonsolvent for) vitamin’
‘ esters, may be employed in lieu of or in conjunc- .
‘ tion with methanol or ethanol. Such solvents
,at'70" C..'40'0 cc. of. ethylene dichloride being used
for each extraction.
The combined extracts ‘
were kept'at 0"v C. overnightand then filtered.
include, among others, isopropanol, n-butanol, .55 The ethylene dichloride was then removed under J
acetone and diacetone alcohol, each of which has
a vacuum. The semi-concentrate thusproduced .
been modi?ed by the addition of‘ at least 9%
was then extracted with methanol in a manner 1
water,ymethanol, and/or ethanol.‘ As previously
pointedyout, a large proportion of the unsaponi- ,
similar to Example I. The following results were ‘
vfled material aside from the vitamin esters is reh- 60 ~
Units‘of' vitamin
deredsoluble in solvents of'the character just de
scribed and consequently the extraction yields a
Vitamin potency of semi-concentrate-____ 785,000
concentrated vitamin ester residue.
Vitamin potency of alcohol .. (methanol
100 grams ofa soup?n shark liver "oil‘contain
ing 63,200 units of vitamin A per gram. were
placed in -a beaker immersed in ice water maintained at a temperature of‘4° C. with ice. 31.2
Aper gram
Vitamin potency of ester
(methanol_‘_ 9
Overall yield of vitamin'A was 9am.
Example 111
grams of 49%‘KOH, sufficient to saponify 82%‘ of 70'
100 grams of ling cod oil'having a'potency of
the glycerides in the 'oil, and 15 grams of water
24,4,000units of vitamin A ‘per gram wererplacedj
(suiiicient'to make the water contentv of the wet
soap produced 25% on completion ‘of the reac-'v - in a-beakerimmersed in ice water'maintained at '
tion) were stirred-in. The reaction mixture was - a temperature of —‘9° C. with ice._ 3% by weight
stirred'io'r-2 hours and then allowed to settle for 75 of isopropanol was added ‘and ‘then su?lcient,
32.7% KOH was added while stirring-to saponlfy ’ ‘render a relatively large proportion of the mate
‘70%: of the-—glyoerides in the oil-,i. e. 35.5 grams ' ' rial other than the vitamin ester and soap formed
of~32.7%- KOH. The mass was stirred for a pe
soluble‘ in a polar solvent,- separatingthe soap
:riod of one hour-and was thereafter stored at 3°
from the u-nsaponi?ecl residue and treating the
C; for -16 hours».-- The average temperature during 5 unsaponi?ed residue with a highly polar selective .
'.-saponi?cation was 1°-G. After storage, the soap
solvent which is characterized by being miscible
was extracted ?ve‘ ‘times with ethylene dichloride
with fat-soluble vitamin‘ alcohols but immiscible
.at 70° C.._» 500cc. of ethylene dichloride were used - ' with —fat soluble vitamin esters to remove'that
tor the ?rst extraction and 300 cc. for successive
portion of the residue soluble therein and produce
extractions.- The combined extracts were kept 1-0 a‘ concentrate high in vitamin ester content.
at;0‘.’. C’. overnight, ?ltered and the ethylene di
2. A process for the production of fat soluble
chloride removed under vacuum; >. The semi-con
vitamin. ester concentrates from vitamin contain
centrate. thus produced 1 was then- extracted with
ing ‘material of marine origin‘ comprisingrpar
methanol as in Examples I and II. The follow
tiallyrsaponifying said material while cooling the
inglresults were obtained:. ..
15 same to below approximately 35° C.- so as to ren=
Units of vitamin
der a relatively large proportion of the material
other than —the vitamin ester and soap formed
.Aper gram
Vitamin potency of -semi-concentrate___ 605,000
Vitamin potency .of ‘alcohol. (methanol
, soluble in a. polar'solvent, separating the. soap
from the unsaponi?ed residue and treating. the
unsaponi?ed residue with a highly polar selective
solvent which is characterizedv by being miscible‘
.. residue)
___ 680,000
fat_soluble ‘vitamin alcohols, but immiscible
Overall yield of vitamin~A was 98.6%. _,
v .
with fat soluble vitamin esters to remove that
portion of the residue soluble therein and pro
>_ 100 grams or. halibut liver oil having a potency 25 duce aconcentrate high'in vitamin ester content.
3. A process for the production of_fat soluble
of 92,500units or'vitamin A per ‘gram were placed
ester concentrates from vitamin contain
inzaibeaigerimmersed in ice water maintained at
ing material.._of- marine origin comprising par:
a temperature of —8° C. with ice. ‘3% by weight '
tially saponifying while cooling the material so
of isopropanol. was added and then ‘su?icient 30 as
to render a, relatively large proportion of the
extract) ____‘___'_ ______________ _______ 256,000 20
Vitamin potency of- ester (methanol
36.8% KOH was added while stirring to saponify
70%_of the glycerides in the oil, 1 .e. 32.6% of
36.8% KOH. The total time of stirring was ,1
material other‘ than the'vitamin ester and soap "
‘formed soluble in methanol, separating the soap
hour, and the average temperature during sapon- _ ' from the unsaponi?ed residuevand treating the '
unsaponi?ed residue with, methanol to remove ‘
i?cationof the'oil' 0° C. v Thereafter the mass was
35 that portion of‘ the'residue soluble therein and.
stpredfor 18__ hours at 3° _C. The scan vWasthen
extracted‘ ?ve times with ethylene dichloride at
produce '_a. concentrate high invitamin ester con-_.
70° ‘C. _ ‘500 ‘cc. of‘ethylene dichloride were used .
.for the ?rst extraction and 300
‘ ‘i. A process} for theproduction of-fatsoluble
cc. forsubsequent :
vitamin .ester concentrates .from .vitamin- con
taining material of marineorigin comprising. par
0°_ C_. ‘overnight and ?ltered. The ethylene die 40 tially‘
saponifying said material while cooling the,
chlqriee, was the; removed. under .vawum- . .The
same'tolbelow approximately 35°C. so as to jre_n"-.
'semie'concent'rate ‘thus produced 'was then ex
,tractedtwitlrmethanol as in the preceding ex_-_ ' dermal‘ relatively large proportion of the material
extractions. ' The combined extracts were kept at
otherzthan the vitamin ester and soap formed
amples. The‘ following resultswere obtained: A 45 soluble'in
methanol, separating the soapifrom'the
'Units-of vitamin ' unsaponi?ecl residue and treating the unsaponi:
?ed residue with methanol to remove that por
tion of the residue soluble therein andproduce
Vitamin potency of semi-concentratelg; 252,000
Vitamin. potency of. valcohol (methanol
- 1
potency -of' ester-(methanol-
- .1 '
5., vAprocess ,for the production of fat soluble
vitamin ester concentrates from vitamin contain-v
ing- material of ‘marine origin comprising par
tially 'saponiiying while cohli'ng the material so as
_________ __,____-___'_ ____ _’___ 320,000
Overallyield of vitamin" A was approximately
a concentratehigh in'vitamin ester, content. ' _ ' '
. 100%.
to render a relatively large proportion of the ma
- Asy'will be noted from the above examples,‘ ‘in
each case the potency ‘of theesterconcentrate
terial other than the vitamin ester and soap
formed soluble in ethanol; separating the soap
producedv was higher than that of the semi-'con- .
. from the 'unsaponi?ed residue and treating the
centrate. ‘In other words, even'with the‘ removal
of the vitamin A alcohol su?icient'methan'ol'sol
unsaponi?ed residue with ethanol to remove that
portion of the residue soluble therein and pro-1 "
uble material was removed so that the potency of_ 60 ducing a concentrate high in’ vitamin esterwcon
the residue was enhanced. As previously pointed
out in-the present speci?cation, it is believed that '
q 6. A process for the production of rat soluble
this 'solubilizatione?’ect on the nonsaponi?ed' and
vitamin ester'concentrates from vitamin contain
nonvitamin material in the ‘semi-concentrate is
ing material of marine origin'compris'ihg' par
probably due to the formation of mono-and di- ,65 _ tially saponifying said material. while cooling the
glycerides during the low temperature saponi
same to belowapproximately- 35". Geo as to ren- .
?cation process of the present invention. ' How-t
der a relatively large proportion of the material
everlit is'not desired to be limited by-this theory‘.
other than the vitamin ester and soap formed sol.Having described our inventio' , what we claim
*uble in ethanol, separating the soap from them
as new and desire to be'secured by Letters Patent 70 saponi?ed" residue and treating the 'unsaponi?ed.
;_ _'1_._‘A process forth‘e production of fat, ‘soluble
vitamin ester concentrates from vitamin contain
ingQmateriaI of marine ori'tin comprising partially
saponipiyinc whilecoolins the material ‘so as to
residuewith ethanolto remove that portion of
‘the residue soluble therein and .produce a con
centrate-high' in vitamin ester content.
, . ._
_> t 7. A process for the. production of fat soluble
e vitamin ester concentrates _f_rom ?sh vliver oils
which comprises partially saponifying a ?sh liver
and produce a concentrate high in vitamin ester
oil while cooling the same to maintain the tem
'9. A process for the production of fat soluble
perature substantially constant during saponi?
vitamin ester concentrates from ‘ vitamin con
cation so as to render a relatively large propor
taining material of marine origin comprising pare
tially saponifying the said material while main
taining the temperature thereof during saponi?
rating the soap from the unsaponi?ed residue and
cation between approximately 0-25° C., separat
treating the unsaponi?ed residue with a highly
ing the. soap from the unsaponi?ed residue and
polar selective solvent which is characterized by
being miscible with‘ fat-soluble vitamin alcohols 10 treating the unsaponi?ed residue with methanol
to remove that portion of the residue soluble
but immiscible with fat soluble vitamin esters to
therein and produce a concentrate high in vita
remove that portion of the residue soluble there
tion of the material other than the vitamin ester
and soap formed soluble in a polar solvent, sepa
in and produce a concentrate high in vitamin
ester content.
min ester content.
8. A process for the production of'fat soluble
vitamin ester concentrates from vitamin contain
ing material of marine origin comprising par
tially saponifying the said material while main
taining the temperature thereof during saponi?ca
tion between approximately 0-25” 0., separating
the soap from the unsaponi?ed residue and treat- .
selective solvent which is characterized by being
miscible with fat-soluble vitamin alcohols but
move that portion of the residue soluble therein
remove that portion of the residue soluble therein
and produce a concentrate high‘ in vitamin ester
ing the unsaponi?ed residue with a highly polar
' immiscible with fat soluble vitamin esters to re
10. A process 101' the production of fat soluble
vitamin’ ester concentrates from vitamin contain
ing materialof marine origin comprising par
tially saponifying the said material while main
taining the temperature thereof during saponi
?cation between approximately 0-25° C., separat
ing the soap from the unsaponi?ed residue and
treating the unsaponi?ed residue with ethanol to.
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