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Патент USA US2412113

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Patented Dec. 3, 1946
Harland‘ H. Young, Chicago, 111., and David
Rubinstein, Brooklinc, Mass., assignors to In
dustrial ‘Patents Corporation, Chicago, 111., a
corporation of Delaware
No Drawing. Application April 14, 1943,
‘Serial No. 483,062
4 Claims.
(Cl. 260-404)
This invention relates tothe purifying of Val
kylolamides and more particularly to the removal
soluble precipitates or, foots separable from the
mixture in any desired manner such as settling,
?ltration, or centrifugal separation. By treat
ing the reaction mixture with the acidic material
kylolamides including mixtures resulting from
reacting fatty or other organic acids oresters 5 in the presence of a small amount of‘ water the
of such acids with alkylolamines in order to proneutralization reaction is facilitated and. other
materials such as the glycerol or other alcohol
duce alkylolamides. Esters of fatty or other orof basic substances from mixtures containing al
ganic ' acids with glycerol or with other m'onohydroxy, dihydroxy or trihydroxy alcohols will
react with alkylolamines to produce reaction 10
which may be present in the mixture are usually
removed as part of the foots.
It is, therefore, the object of the present in-.
mixtures in which a large number of compounds
exist in‘ equilibrium. This reaction,‘ if carried
vention to remove basic and other impurities
from mixtures containing alkylolamides so as
on in theand
under of
an excess
of the condialkyl-
to Another
produce puri?ed
object of
the inventionxis
to . provide
- 1:
tions can be made to consist predominantly of 15 a process by which basic impurities are removed
from crude alkylolamides as an insoluble precipi
alkylolamides of the acids. Similarly, reaction
mixtures can be produced by reacting the acids
Another object of the invention is to provide
themselves with alkylolamines. Thus by reacting alkylolamines with fatty acids an equilibrium
a process of purifying alkylolamides containing
mixture is produced containing the fatty acids, 20 basic impurities by the employment of‘ acidic
the alkylolamine, alkylolamine- soaps, alkylolmaterials forming insoluble precipitates or foots.
amine esters, alkylolamides and alkylolamide
Another object of the invention is to provide a
process of purifying alkylolamides of fatty acids
esters. If the reaction is carried on between an
alkylolamine and esters of fatty acids, the reacin which strong mineral acids or compounds of
tion mixture may also contain the ester as well 25 such acids with weak bases are employed to form
insoluble precipitates with basic reacting impuri
as the alcohol of the ester. Other by-products
of unknown structure may exist but such by-
; I .
products are in general basic in reaction because
A further object of the invention is to provide
a process of purifying alkylolamides of fatty
of free nitrogen functions.
The present invention is directed to removing 30 acids containing basic impurities in which the
the basic impurities in such mixtures and is paralkylolamides are dissolved in an inert solvent
ticularly applicable to reaction products between
and the impurities are neutralized to form com
glycerides of higher fatty acids such as vegetable
pounds insoluble in the solvent.
or animal oils and either mono-alkylolamines or
A still further object of the invention is to
dialkylolamines. By reacting the glyceride with 35 provide a process of purifying alkylolamides 0011
an alkylolamine in the presence of an excess of
taining basic impurities in ‘which a solidvacid
the alkylolamine a reaction’ mixture consisting
reaction material is employed to remove such
fatty acids can be produced which alkylolamides
The preferred practice of the present invention
exist in equilibrium with . alkylolamine, glycer- 40 includes the addition of a strong mineral acid in
ides, glycerol, alkylolamine soaps and alkylol-
‘a small quantity of water to the reaction prod
amine esters as well as alkylolamide esters.
nets of an alkylolamine and a glycerol ester of
the reaction is with a dialkylolamine‘ there are‘
higher fatty acids which reaction products con-1
also other possible reaction products such as the
tain basic impurities such as the alkylolamine,
dialkylolamine monoacid ester and the dialkyl- 45 alkylolamine esters, alkylolamine ‘soaps, etc.
Sufficient acid is preferably added and thor
olamide monoacid ester. The basic reacting
materials, among Which arealkylolamine soaps,
oughly admixed with the reaction products to
excess alkylolamine and alkylolamine esters
neutralize all of the basic impurities. A precipi
cause the reaction products to develop off ?avors
tate forms which is insoluble in the alkyolamides
and odors which deleteriously affect the mixtures 50 or any glycerol esters or alkylolamide esters
for use in edible and other products” It has been
which are present. This precipitate in most'
found that substantially all of the materials
cases readily settles and can be removed by de.-.
causing such deleterious flavors, or odors, can
canting the alkylolamides or by ?ltration or’cen
be removed from the mixture by neutralization
trifugal separation. This precipitate is generallyv
with an acidic material which willproduce in-, 55 ?occulent and resembles, the foots.._obtained. in
the re?ning of ordinary vegetable and animal
re?ning agent. Many other acid reacting mate
rials such as lower fatty acids neutralize the
fats or oils. If the alkylolamide is to be incorpo
alkaline impurities in the reaction mixtures above
rated in glyceride oils, which is many times the
referred to but yield compounds which retain
case, the crude alkylolamide may be added to the
glyceride oil prior to re?ning in accordance with (a their solubility in the mixture, which compounds
cannot be easily removed from the mixture. The
the present. invention. Thus the glyceride oil
invention, therefore, is concerned with the em
or fat functions as a solvent for the alkylolamide
ployment of acids or acidic materials which form
during the re?ning operation and assists in sep
arating the precipitate from the alkylolamides as ~ insoluble precipitates with the basic impurities,
this precipitate is also insoluble in the glyceride 10 mineral acids or their salts with weak bases being
the preferred acidic material, but any acid react
oil. Any alkylolamide esters present are also re
' ing-material either organic or inorganic which is
tained in the glyceride oil and‘are not objection
sufficiently acid'to neutralize the basic materials
able. The temperature of re?ning will vary with
and which produces insoluble foots which may be
different alkylolamides depending upon the al
removed from the reaction mixture may be em
kylolamine employed or the fatty acids present
ployedin the present invention. Materials other
in the alkylolamide and upon the nature of the
than strong acids which are contemplated for use
glyceride oil solvent, if one is employed. In gen
in the invention include sodium dihydrogen phos
eral the temperature should be suiiiciently high
to render ?uid the crude reaction mixture or
phate, sodium acid sulphate, potassium acid tar
the glyceride oil in which it is incorporated. 20 trate and aluminum sulphate. Other salts of like
nature ,andedible could also be used.
Thus, when re?ning alkylolamides or alkylol
While the invention has been speci?cally de
amides admixed with glyceride oils containing
scribed with respect to reaction mixtures pro
substantially saturated fatty acid radicals, such
duced by reacting an alkylolamine with a. glycerol
materials should be'heated to a temperature
sui’?ciently’ above the melting point to render 25 ester of higher fatty acids, it is also applicable to
re?ning of reaction mixtures of alkylolamines
them ?uid prior to the re?ning operation. Thus
with the fatty acids themselves, with esters other
the temperatures employed may range between
than the glycerol esters of fatty acids, acid an
approximately 70° F. and 180° F. although in
- hydrides, acid chlorides, or other acylating agents
some cases higher temperatures may be desir
30 all of which acylating agents are included in the
term lypophyllic acylating agents. In general it
The preferred reagent is phosphoric acid in a
is desired to remove all of the materials in the
concentration‘between approximately 50% and
reaction mixture which have a, free nitrogen
90%, as such phosphoric acid also makes it pos
function which includes any alkylolamine present
sible to selectively remove the impurities. Thus,
or the alkylolamine esters. Any alkylolamine
the alkylolamine phosphate is somewhat more
soaps are also decomposed to liberate the amine
insoluble than the alkylolamine ester phosphate
so thatthe amine portion of such compounds
and. can be selectively precipitated to remove it
may likewise be removed from the mixture. Also,
from either the alkylolamide alone or from the,
alkylolamide dissolved in a glyceride oil or other
glyceride oils or fats have‘been described as a
ester of a. higher fatty acid. By adding just 40 solvent for the reaction material during the re?n
ing operation. It will be apparent that any inert
slightly more phosphoric acid solution than that
solvent for the alkylolamides being treated may
necessary to react with the alkylolamine, this
be employed.‘ The foots produced by the re?ning
material can be substantially completely removed
operation may be removed from such admixtures
from the mixture after which additional phos
phoric acid solution can be added to precipitate 45 by ?ltration, decantation or centrifugal separa
tion and other impurities such as coloring matter,
the alkylolamine ester phosphate. Other strong
mineral acids such as sulfuric and hydrochloric
acids in substantially the same concentration
referred to above can, however, be employed to
remove the basic impurities from the ialkylol
Other acid reacting materials "may. also be em
ployed to remove basic impurities. For example,
various salts of strong acids such as sulfuric, hy
drochloric, and phosphoric with weak bases in r
the form of granular salts can be employed as
?lters through whichthe crude alkylolamide mix
ture is passed. The admixture of a small amount
of moisture or Water with the crude. alkylolamide
etc., are to a large extent removed with the foots
by adsorption thereon.
While we have described the preferred embodi
ments of our invention, it is understood that the
details thereof may be varied within the scope of
the following claims.
We claim:
1. The method of purifying alkylolamides asso
ciated with other reaction products formed in
reacting alkylolamines with fatty acids and their
esters and containing alkylolamides, and other
basic substances of bitter ?avor, which comprises
treating thecrude alkylolamides with‘ an aqueous
mixture facilitates the removal ofthe basic im 60 solution of a mineral acid material in a glyceride
solvent for said alkylolamides and alkylolamine
purities. 'It ~is-also possible to suspend such acid‘
esters to neutralize said basic substances and to
reacting salts by agitation in the crude mixture
‘or-crude mixture combined with a solvent, and
allow the same to settle. Such operation causes
precipitate the same as insoluble compounds,
the basic ingredients of the crude mixture to
react with the salts andinsolu-ble products formed
thereby to be removed from the mixture. The
dampening of the granular vsalt with a small
amount of water prior to admixing the same with
highduring the treatment to render'the solution
of .alkylolamides in a liquid condition and there
after separating said compounds from the puri?ed
while maintaining the temperature su?icien-tly
2. The method of purifying crude alkylolamides
the mixture to be re?ned or the addition of a
of higher f-at-tyacidsformed by reacting an excess ‘
small .amount ‘of Water to the ‘mixture during
re?ning ‘with the granular material assists in the
reaction with'the basic materials. It is apparent
that concentrated solutions or .s'lurri'es of such
acid reactingsalts may also be employed as ya 75
of ' alkylolamines with higher‘ fatty acids and
glycerides thereof, said crude alkylolamides con
taining alkylolamides, and other side reaction
products of a basic nature and having a bitter ‘
?avor, which’ comprises contacting a solution of
said crude alkylolamides in a glyceride oil with
3. The method according to claim 2 in which
an aqueous solution of a neutralizing agent conthe neutralizing agent is aqueous phosphoric acid
taming a mineral acid to convert said basic subof about 50% ‘to 90% concentration.
stances into insoluble salts, supplying su?icient
‘i. The method according to claim 2 in which
heat during the operation to keep the solution of 5 the glyceride oil is triglyceride fat.
alkylolamides in a liquid condition and then sepa
rating said insoluble salts from the solution of
puri?ed alkylolamides.
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