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Патент USA US3094568

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United States Patent 0 ice
3,094,555
Patented June 18, 1963
1
2
3,094,555
Useful improvements in ?nal detergent odors were ob
served at the following levels:
Percent
PURIFICATION OF SODIUM ISETHIONATE
Vincent Lamberti, Hackensack, and Robert A. Haass,
Fort Lee, NJ., assignors to Lever Brothers Company,
New York, N.Y., a corporation of Maine
No Drawing. Filed Aug. 3, 1959, Ser. No. 831,026
12 Claims. (Cl. 260-513)
Sodium hypochlorite ________________________ __ 0.12
Sodium chlorite ____________________________ __ 0.05
Calcium hypochlorite _______________________ __ 0.12
Potassium persulfate ________________________ __ 0.42
Potassium monopersulfate ___________________ __ 0.25
This invention is concerned with a process for the puri
?cation of sodium isethionate. In particular, it is con 10 The above results were obtained using commercial sodium
cerned with a process for treating sodium isethionate so
isethionate which analyzed approximately 0.02% reducing
that when the materials is subsequently used in the syn
thesis of a detergent, the resulting detergent will not have
material calculated as sodium sul?te. For sodium isethio
nate containing higher levels of reducing impurities, high
er levels of oxidizing agents are required. For example,
Sodium isethionate is generally prepared commercially 15 in the case of sodium isethionate to which 0.4% sodium
sul?te was deliberately added, sodium hypochlorite was
by the reaction of ethylene oxide and sodium bisul?te.
required in an amount su?icient to oxidize all the added
U.S. Patent 2,810,747 discloses a method of carrying out
sodium sul?te plus 0.2% excess. When the original level
the reaction so as to minimize impurities by careful selec
of reducing materials in the sodium isethionate is un
tion of reaction conditions. Sul?te and bisul?te impurities
can be removed readily from sodium isethionate prepared 20 known, the amouut of oxidizing agent required to purify
the material can be determined by ?rst analyzing the sam
by methods other than that of the patent. For example,
ple for reducing materials, for example, by means of an
they are removed by evaporation of a 40-45% aqueous
iodine titration.
solution of the material at atmospheric pressure in a
In general, there is no advantage in using any of the
heated sigma blade mixer, producing a dry powder con
taining no reducing material detectable by iodine titra 25 oxidants of the present invention in an amount over 1%.
Use of excessive amounts of oxidant, besides being un
tion. Alternatively, the sodium isethionate solution is
economical, has the disadvantages of causing a destruc
treated with a low level (less than 1%) of oxidizing
tion of the isethionate and a darkening of color.
agents such as sodium hypochlorite and then evaporated
Of the oxidizing agents useful in the present process,
to dryness. Again, iodine titration shows no reducing im
purities to be present.
30 sodium hypochlorite is preferred. Sodium isethionate
treated according to the present invention with sodium
'The avoidance or removal of sul?te and bisul?te im
hypochlorite may be converted into acyl isethionate deter
purities, however, does not prevent the sodium isethionate
material from producing an objectionable odor when it
gents which have a very clean odor and which retain such
an undesirable odor.
is converted to a detergent. 0n the contrary, even though
a. clean odor for a longer time than is the case when other
the sodium isethionate has been prepared or treated so 35 oxidizing agents have been used.
The following examples are given solely for purposes
that it contains no detectable sul?te or bisul?te, when that
sodium isethionate is converted to a detergent, the deter
for illustration and ‘are not to be considered as limiting
gent may have a disagreeable odor. The absence of sul
the invention to ‘these embodiments. Many modi?cations
?te or bisul?te in a ?nished sodium isethionate powder
will be apparent to those skilled in the art without de
of itself is not su?icient to assure that the detergent pre 40 parting from the spirit or scope of the invention.
pared therefrom will possess a clean odor.
EXAMPLE 1
According to the present invention, odor causing im<
purities are removed from sodium isethionate by treating
Preparation of Acyl Isethiomrte Detergents
the material with certain oxidizing agents. Not all oxidiz
ing agents bring about the desired result. Good results 45 All acyl isethionate samples discussed in the examples
are obtained with sodium hypochlorite, sodium chlorite,
below were prepared in pilot plant equipment according
calcium hypochlorite, potassium persulfate and potassium
to the following procedure: 10.7 lbs. of sodium isethio
monopersulfate. Most surprisingly, however, hydrogen
hate was heated to 108° C. in a 10 gal. jacketed, stainless
peroxide does not yield good results, and neither does
steel, sigma blade mixer using 30 lb. steam. 14.85 lbs.
sodium perborate or sodium nitrate. Sodium nitrate has 50 of coconut fatty acid chloride (prepared from iodine
the additional disadvantage of producing a darkening of
value = 5 coconut fatty acids and phosphorous trichloride)
the treated material.
was then added and the mixture was heated until the reac—
'The sodium isethionate is first treated to remove what
tion (evolution of HCl) ensued and the temperature rose
ever sul?te or bisul?te impurities are present, and is then
to 130° C. The steam was then shut off and mixing was
subjectal vto treatment with an oxidizing agent according 55 continued until the temperature fell to 90° C. The pH
to the present invention. The minimum level of oxidizing
(10% solution in distilled water at 35° C.) or the result
agent required varies somewhat depending upon the par
ing powdery reaction product was’ then adjusted 'to 7.2 by
ticular oxidizing agent used and upon the level of odor
slowly adding approximately 180 grams of 50% sodium
causing impurities which are present in the sodium
hydroxide. Aiter mixing for ‘an ‘additional ten minutes,
isethionate. The lowest ‘level of oxidizing agents which 60 the batch was cooled to 40° C. by passing tap water
have given very good, clean odors in the ?nal detergent
through the mixer jacket. The batch was then discharged
are as follows, the percentages referring to the weight of
and sampled for an odor evaluation. The overall time
treated sodium isethionate:
'cycle for each preparation was about one hour.
Percent
Sodium hypochlorite ________________________ __ 0.24
Sodium chlorite ____________________________ __ 0.1
Potassium persulfate ________________________ __ 1.0
Potassium monopersulfate ___________________ __ 0.5
The odor evaluation was carried out on a water slurry
65 of the acyl isethionate detergent samples (about one tea
spoon of each) in a clean odor-free disposable paper cup.
The slurry was prepared and smelled by the tester in a
special odor testing room to avoid interference from for
3,094,555
4
3
eign odors. The results were credited according to the
acyl isethionate detergent was moderately improved (“2"
following system: A rating of “1" was assigned to a
sample which had a satisfactory clean odor. A rating of
“2” meant that the sample had an acceptable odor, i.e.
rating) compared to the control.
a tolerable level of odor which can be masked satisfactor
ily ‘with perfume. A rating of “3” was given to samples
which had an odor level too strong to be masked by
EXAMPLE 8
Or
Use 0)‘ Potassium Persulfate‘
54.5 grams of potassium persulfate (100%) was added
to a solution of 12 lbs. of sodium isethionate in 16.6 ‘lbs.
perfume.
of water; i.e., 1.0% K2S2O8 basis sodium isethionate.
In Examples 2 through 9 cited below the same lots of
‘fatty acid chloride and sodium isethionate were used in
order to obtain a comparison of the elfectiveness of the
Approximately 48 grams of 50% sodium hydroxide was
‘added to this solution during the subsequent evaporation
step in order to maintain the pH between 8 and 9. The
dried sodium isethionate was then converted into acyl
various oxidizing agents.
isethionate detergent according to the procedure described
EXAMPLE 2
in Example 1. The odor of the acyl isethionate detergent
Acyl isethionate detergent was prepared as described 15 was noticeably clean and rated “1.”
in Example 1 ‘above from regular commercial sodium
EXAMPLE 9
isethionate. The odor of the resulting detergent was given
the rating of “3," and the material had a smell of burnt
Use of Potassium Monopersulfate
rubber.
59 grams of 44.6% active potassium monopersulfate
EXAMPLE 3
(trademark Oxone) was dissolved in a solution of 12
Acyl isethionate detergent was prepared as described in
lbs. of sodium isethionate in 16.6 lbs. of water; i.e., 0.5%
Example 1 from commercial sodium isethionate which
KHSO5 basis sodium isethionate. Thirty grams of 50%
had ?rst been dissolved in water to form a 42% aqueous
sodium hydroxide was added during the subsequent evap
solution and then evaporated to dryness before reacting
oration step in order to maintain the pH between 8 and 9.
with the acid chloride. The odor of the resulting de
The dried sodium isethionate was then converted into
tergent was still given the rating of “3” and the ma?trial
acyl isethionate detergent according to the procedure
still had a burnt rubber odor. This experiment shows that
described in Example 1. The odor of the acyl isethionate
in the absence of treatment with a suitable oxidizing agent
detergent was noticeably clean and rated “1.”
according to the present invention, simple evaporation of 30
EXAMPLE 10
an aqueous solution of sodium isethionate, even though it
Use of Potassium Monopersulfate
is sufficient to remove the sul?te and bisul?te impurities,
does not lead to a clean or improved odor in the ultimate
123 grams of 44.0% active potassium monopersulfate
detergent.
(trademark Oxone) was dissolved in a solution of 12
EXAMPLE 4
lbs. of sodium isethionate in 16.6 lbs. of water; i.e., 1.0%
Use of Sodium Hypochlo'rite
240 grams of 5.25% sodium hypochlorite solution was
added to a solution of 12 lbs. of sodium isethionate in
KHSO5 basis sodium isethionate. Fifty-seven grams of
50% sodium hydroxide was added during the subse
quent evaporation step in order to maintain the pH be
tween 8 and 9.
The dried sodium isethionate was then
16.6 lbs. of water; i.e., of 0.23% NaOCl basis sodium 40 converted into acyl isethionate detergent according to
isethionate. The resulting solution was then evaporated
the procedure described in Example 1. The odor of
to dryness at atmospheric pressure in ‘a 10 gal. sigma
the acyl isethionate detergent was noticeably clean and
blade, stainless steel mixer using 40 lb. steam on the
rated “1,” as compared with a “2” rating and a burnt
jacket. 10.7 lbs. of the resulting dry sodium isethionate
characteristic for the product made from the same lot of
was then converted to acyl isethionate detergent accord
sodium isethionate, but which was not treated in accord
ing to the procedure described in Example 1. The odor
ance with the invention.
of the acyl isethionate detergent was noticeably clean and
EXAMPLE 11
rated “1.”
EXAMPLE 5
Use of Potassium Monopersulfat‘e
Use of Sodium Hypochlorite
30.0 grams of 44.0% active potassium monopersul
50
fate (trademark Oxone) was dissolved in a solution of
The procedure of Example 4 was repeated, but 1%
8.0 grams of sodium hydroxide in 240 grams of water.
NaOCl (basis sodium isethionate) was used. The odor
This solution (i.e., 0.25% KHSO5 basis sodium isethio
of the resulting detergent was noticeably clean and
nate) was then added to a soluution of 11.6 lbs. of sodium
rated “1.”
EXAMPLE 6
55 isethionate in 16 lbs. of water. The combined solutions
were evaporated to dryness. The dried sodium isethio
Use of Sodium Chlorite
nate was then converted to acyl isethionate detergent ac
cording to the procedure described in Example 1. The
Eight grams of sodium chlorite (100%) was dissolved
odor of the acyl isethionate detergent was moderately
in 148 grams of water containing 3 grams of sodium
hydroxide. This solution was then added to 12 lbs. of 60 improved and rated “2” with a slight burnt characteristic,
as compared with a “3” rating and a strong burnt rubber
sodium isethionate dissolved in 16.6 lbs. of water; i.e.,
characteristic for the product made from the same lot
0.15% NaClOz basis sodium isethionate. After the re
of sodium isethionate, but which was not treated in ac
sulting solution was evaporated to dryness, the sodium
isethionate was converted to acyl isethionate detergent as
described in Example 1 above. The odor of the acyl
isethionate detergent was noticeably clean and rated “1.”
EXAMPLE 7
cordance with the invention.
What is claimed is:
1. A process for removing odor causing impurities
from sodium isethionate which has been prepared by the
reaction of ethylene oxide and sodium bisul?te, said proc
Use of Calcium Hypachlorite
ess comprising removing whatever sul?te and bisul?te
40.8 g. of 30.2% active calcium hypochlorite was added 70 impurities are present, and treating the sodium isethionate
with an oxidizing agent selected from the group con
to a solution of 12. lbs. of sodium isethionate in 16.6 lbs.
of water; i.e., 0.23% ca. (OCDZ basis sodium isethionate.
After the resulting solution was evaporated to dryness,
sisting of sodium hypochlorite, sodium chlorite, cal
cium hypochlorite, potassium persulfate and potassium
the sodium isethionate was converted to acyl isethionate
monopersulfatc, each of said oxidizing agents, when se
detergent as described in Example 1. The odor of the
lected, being present in the following minimum percent
3,094,555
5
6
ages by weight of sodium isethionate: sodium hypochlo
rite-0.12%, sodium chlorite—-0.0S%, calcium hypochlo
reaction of ethylene oxide and sodium bisul?te, said
process comprising treating the sodium isethionate with
rite-0.12%, potassium persulfate——0.42%, and potas
sium monopersulfate—0.5%, said oxidizing agent being
sodium chlorite in an amount sufficient to oxidize what
ever suliite and bisul?te impurities are present, and with
at least an excess of 0.05% based on the weight of the
present in a maximum amount of about 1%.
2. A process for removing odor causing impurities
sodium isethionate, said sodium chlorite being present
in a maximum amount of about 1%.
from sodium isethionate which has been prepared by the
8. A process for removing odor causing impurities
reaction of ethylene oxide and sodium bisulfite, said proc
from sodium isethionate which has been prepared by the
ess comprising treating sodiiun isethionate which is sub
stantially free of sul?te and bisul?te impurities with an 10 reaction of ethylene oxide and sodium bisul?te, said proc
ess comprising treating the sodium isethionate with cal
oxidizing agent selected from the group consisting of so
dium hypochlorite, sodium chlorite, calcium hypochlo
rite, potassium persulfate and potassium monopersulfate,
each of said oxidizing agents, when selected, being pres
ent in the following minimum percentages by weight of
sodium isethionate: sodium hypochlorite—0.l2%, so
dium chlorite—-0.05%, calcium hypochlorite—0.12%,
potassium persulfate—0.42% and potassium monoper
sulfate-0.5%, said oxidizing agent being present in a
maximum amount of about 1% .
3. A process for removing odor causing impurities
from sodium isethionate which has been prepared by
the reaction of ethylene oxide and sodium bisul?te, said
process comprising treating the sodium isethionate with
sodium hypochlorite in an amount suf?cient to oxidize
whatever sul?te and bisulfite impurities are present, and
with at least an excess of 0.12% based on the weight of
the sodium isethionate, said sodium hypochlorite being
present in a maximum amount of about 1% .
4. A process for removing odor causing impurities
from sodium isethionate which has been prepared by the
reaction of ethylene oxide and sodium bisul?te, said proc
ess comprising treating the sodium isethionate with sodi
um hypochlorite in an amount su?icient to oxidize what
ever sul?te and bisul?te impurities are present, and with
at least an excess of 0.24% based on the weight of the
cium hypochlorite in an amount sufficient to oxidize
whatever sul?te and bisul?te impurities are present, and
with at least an excess of 0.12% based on the weight of
the sodium isethionate, said calcium hypochlorite being
present in a maximum amount of about 1%.
9. A process for removing odor causing impurities
from sodium isethionate which has been prepared by the
reaction of ethylene oxide and sodium bisul?te, said proc
ess comprising treating the sodium isethionate with po
tassium persulfate in an amount su?icieut to oxidize
whatever sul?te and bisulfite impurities are present, and
with at least an excess of 0.42% based on the weight of
the sodium isethionate, said potassium persulfate being
present in a maximum amount of about 1%.
10. A process for removing odor causing impurities
from sodium isethionate which has been prepared by the
reaction of ethylene oxide and sodium bisul?te, said proc
ess comprising treating the sodium isethionate with po
tassium monopersulfate in an amount su?icient to oxidize
whatever sul?te and bisul?te impurities are present, and
with at least an excess of 0.5% based on the weight of
the sodium isethionate, said potassium monopersulfate
being present in a maximum amount of about 1%.
11. A process for removing odor causing impurities
from sodium isethionate which has been prepared by the
sodium isethionate, said sodium hypochlorite being present
reaction of ethylene oxide and sodium bisul?te, said proc
ess comprising treating sodium isethionate which is sub
5. A process for for removing odor causing impurities
stantially free of sul?te and bisul?te impurities with po
from sodium isethionate which has ‘been prepared by the 40 tassium monopersulfate in an amount at least 0.5% based
reaction of ethylene oxide and sodium bisul?te, said proc
on the weight of the sodium iscthionate, said potassium
ess comprising treating sodium isethionate which is sub
monopersulfate being present in a maximum amount of
about 1
stantially free of sul?te and bisul?te impurities with so
dium hypochiorite in an amount at least 0.12% based
32. A process for removing odor causing impurities
on the weight of the sodium isethionate, said sodium
from sodium isethionate which has been prepared by the
hy-pochlorite being present in a maximum amount of
reaction of ethylene oxide and sodium bisul?te, said proc
about 1% .
ess comprising treating sodium isethionate which is sub
6. A process for removing odor causing impurities
stantially free of sul?te and bisul?te impurities with po
from sodium isethionate which has been prepared by the
tassium monopersulfate in an amount at least 0.25%
reaction of ethylene oxide and sodium bisul?te, said proc 50 based on the weight of the sodium isethionate, said po
ess comprising treating sodium isethionate which is sub
tassium monopersulfate being present in a maximum
stantially free of sul?te and bisul?te impurities with so
amount of about 1%.
in a maximum amount of about 1%.
dium hypochlorite in an amount at least 0.24% based
on the weight of the sodium isethionate, said sodium hy
pochlorite being present in a maximum amount of about 55
1%.
7. A process for removing odor causing impurities
from sodium isetbioriate which has been prepared by the
References Cited in the ?le of this patent
UNITED STATES PATENTS
2,804,466
2,806,876
2,810,747
Schurman __________ __ Aug. 27, 1957
Blaser et al ___________ __ Sept. 17, 1957
Sexton et al. ________ __ Oct. 22, 1957
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