Note: Descriptions are shown in the official language in which they were submitted.
, 10~9zg5
BACKGROUND OF THE INVENTION
The present invention is related to an improved method
for making aliphatic diperoxyacids having from about 12 to
about 20 carbon atoms.
Peroxygen bleaching agents in general and peroxyacid
compounds in particular have long been recognized as effective
bleaching agents for use when the adverse color and fabric
damage effects of harsh halogen active bleaching agents cannot
be tolerated. See, for example, Canadian Patent 635,620, issued
January 30, 1962 to McCune. This attractive nature of
peroxyacid compounds makes it desirable to be able to make
them in the most economical manner.
The prior art teaches the making of peroxyacid compounds
in several ways. Parker et al. in Journal American Chemical
-
Society, 79, 1929 ~1957), disclose making diperoxyacids by
dissolving a dibasic acid in sulfuric acid and adding hydrogen
peroxide dropwise. U.S. Patent 3,079,411, February 26, 1963,
to Silbert et al., discloses forming long chain aliphatic
peroxyacids by combining an aliphatic acid with an alkanesul-
fon~c acid and then treating the combination with an excess of
hydrogen peroxide. U.S. Patent 2,813,896, November 19, 1957,
to Krimm, discloses forming peroxyacids by combining sulfuric
acid and hydrogen peroxide and subsequently treating the
combination with carboxylic acid. The reaction is conducted
so that there is at least one mole of sulfuric acid present at
the end of the reaction for every six moles of water.
While the prior art teaches several methods for making
peroxyacids, it does not indicate what problems are involved
with making long chain peroxyacids. It has been found that -
using the prior art methods~ such acids are formed slowly or ;~
in very small,difficult to filter crystals.
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-- 10'79'~9S
It is an object of the present invention to provide a
method for making diperoxyacids which overcomes the above
problems. Specifically, the present invention provides a
method whereby diperoxyacids can be made much quicker than prior
art methods or in larger, easier to filter crystals.
These and other objects of the present invention will
become apparent from the following description.
All percentages and ratios used herein are by weight -
unless otherwise specified.
SUMMARY OF THE INVENTION
The present invention relates to a process for
making aliphatic diperoxyacids comprising adding a dibasic
acid having from about 12 to about 20 carbon atoms to a
solution containing from about 6% to about 14% hydrogen
peroxide, about 69% to about 82% sulfuric acid and about 6%
to about 21% water.
DETAILED DESCRIPTION OF THE INVENTION
The process of the present invention involves the
following steps:
A. Forming a solution containing from about 6% to about
14% hydrogen peroxide, about 69% to about 82%
sulfuric acid and about 6% to about 21% water.
B. Adding to the solution of A an aliphatic
dibasic carboxylic acid having the formula
O O `
Il 11
HO - C - R - C - OH
wherein R is an alkylene group having from about 10
to 18 carbon atoms to form a mixture. In a preferred
process the diperoxyacid is added slowly over a time
period of from about 30 to about 120 minutes.
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: ~ . . : ,:
107~Z~5
C. Maintaining the mixture of B at a temperature of
from about 10C to about 50C until the diperoxyacid
crystals are formed. Preferably- the mixture is
maintained at the desired temperature for a period of
from about 1 to about 4 hours after all of the dibasic
acid has been added.
D. Recovering the diperoxyacid crystals of step C by
means of filtration.
E. Washing the crystals with water and drying said ~ - -
crystals.
The diperoxyacid formed using the above-described
method is formed quickly and under certain conditions (e.g~, low
temperature, slow addition of the dibasic acid, and/or small
amount of hydrogen peroxide~ the crystals formed are u~ry
easily filtered. The method also provides for a safer, more
easily controlled reaction since the strongly exothermic mixing
of hydrogen peroxide, water and sulfuric acid can be done
;~ before the unstable diperoxy acid is formed. For example, the
mixing of the three liquid components can be done in a vessel
separate from the one in which the diperoxyacid IS formed.
The ingredients used in the process of the present
invention are all readily available in commerce. Hydrogen ;
peroxide can be of any concentration, but is preferably from
about 35% to about 70%, while sulfuric acid is preferably used ~
in a concentration of from about 92% to about 98~. The ~-
percentages of these materials in the reaction mixture described
above are based on pure materials.
The acids suitable for use herein are those aliphatic
dibasic carboxylic acids having from about 12 to about 20
carbon atoms. The unsubstituted acids have the following
general formula:
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1079Z9S
o o ::
Il 11 .
HO - C - R - C - OH -
wherein R is an alkylene group containing from about 10 to
about 18 carbon atoms. Preferred R groups are of the formula ;-
- ~CH2~n- wherein n is a nur[lber of from about 10 to about 14.
Especially preferred is dodecanedioic acid (n = 10).
~ hile it is true as indicated above that the levels of
water, sulfuric acid and hydrogen peroxide can be within the
ranges given, there exist preferred ranges for these three -
materïals which vary with the chain length of the aliphatic
10 dibasic acid employed. These ranges are shown below for some
of the preferred acids.
% Sulfuric % Hydrogen
Acid % Water Acid Peroxide
O O
Il 11 ~-
2~10 16--21 69-75 8-14
O O
Il 11 .
2~ 11 9-14 76-80 8-14
O O
HO - C ~(CH2~12- C --OH 8--13 78-82 8-14
In a preferred method the water and hydrogen peroxide are
~mixed together, cooled to about 5C to about 15C and the
sulfuric acid is added dropwise.
The amount of dibasic acid used in the present process
varies with the actual amount of hydrogen peroxide used. The
relationship is as follows:
O O
ll ll 2 4
HO - C - (CH2~n ~ C - OH ~ 2H22 < --
O O
Il 11
HOO - C - ~CH2~n - C - OOH + 2H2
. - - . . : - . .
gz,~5
It is preferred, however, that hydrogen peroxide be used in
an amount which is 25% or more în excess of the stiochiometric
amount required.
The peroxyacids made using the process of the present
invention can be dried using conventional drying techniques
with usual safeguards for handling peroxyacids being observed.
Compositions Containing the Peroxyacid Compounds
The peroxyacid compounds made using the process of the
present invention can be used in a wide variety of compositions.
A preferred use is as a fabric bleaching agent. To insure that
compositions containing the peroxyacid compounds are safe and
effective, certain additives are desirably present.
It is well documented in the peroxyacid literature that
peroxyacids are susceptible to a number of different stability
problems, as well as being likely to cause some problems.
Looking at the latter first, peroxyacids decompose exothermally
and when the material is in dry granular form the heat generated
must be controlled to make the product safe. The best exotherm
control agents are those which are capable of liberating moist-
ure at a temperature slightly below the decomposition temper-
ature of the peroxyacid employed. U.S. Patent 3,770,816, ;
; issued November 6, 1973 to Nielson, discloses a wide variety
of hydrated materials which can serve as suitable exotherm
control agents. Included among such materials are magnesium
sulfate 7H2O, magnesium formate dihydrate, calcium sulfate -
(CaSO4 2H2O), calcium lactate hydrate, calcium sodium sulfate
(CaSO4 2NA2SO4 2H2OI, and hydrated forms of such things as
sodium aluminum sulfate, potassium aluminum sulfate, ammonium -~
aluminum sulfate and aluminum sulfate. Preferred hydrates are
the alkali metal aluminum sulfates, particularly preferred is
potass-ium aluminum sulfate. Other preferred exotherm control
agents are those materials which lose water as the result of
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1079Z9S
chemical decomposition such as boric acid, malic acid and
maleic acid. The exotherm control agent is preferably used
in an amount of from about 100~ to about 200% based on the -
weight of the peroxyacid compound.
The other pro~lems faced when peroxyacid compounds are
used fall into the area of maintaining good bleach effectiveness.
It has been recognized that metal ions are capable of serving
as catalyzing agents in the degradation of the peroxyacid
compounds. To overcome thïs problem chelating agents can be
used in an amount ranging from 0.005% to about 1.00~ based on
the weight of the composition to tie up heavy metal ions. U.S.
Patent 3,442,937, May 6, 1969, to Sennewald et al., discloses
a chelating system comprising quinoline or a salt thereof, an
alkali metal polyphosphate and, optionally, a synergistic amount
of urea. U.S. Patent 2,838,459, June 10, 1958, to Sprout, Jr.,
discloses a variety of polyphosphates as stabilizing ag,ents
for peroxide baths. These materials are useful herein as
stabilizing aids. U.S. Patent 3,192,255, June 29, 1965,-to
Cann~ discloses the use of quinaldlc acid to stabilize
percarboxylic acids. This material, as well as picolinic
acid and dipicolinic acid, would also be useful in the
compositions of the present invention. A preferred chelating
system for the present invention is a mixture of 8-hydroxy-
quinoline and an acid polyphosphate, preferably acid sodium
pyrophosphate. The latter can be a mixture of phosphoric acid
and sodium pyrophosphate wherein the ratio of the former to
the latter is from about 0.5:1 to about 2:1 and the ratio of
the mixture to 8-hydroxyquinoline is from about 1:1 to about
5:1.
In addition to the above-mentioned chelating systems to
tie up heavy metals in the peroxyacid compositions, coating
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107929~
materials may also he used to extend the shelf life of dry
granular compositions. Such coating materials may be, in
general, acids, esters, ethers and hydrocarbons and include
such things as wide varieties of fatty acids, derivatives of
fatty alcohols, such as esters and ethers, derivatives of
polyethyleneglycols such as esters and ethers and hydrocarbon
oils and waxes. These materials aid in preventing moisture
from reaching the peracid compound. Secondly, the coating
material may be used to segregate the peracid compound from
other agents which may be present in the composition and
adversely affect the peracid's stability. When used in this
manner the coating may be used on ~oth the peracid compound
and the other agent or either individually. me amount of the - -
coating material used is generally from about 2.5% to about
15% based on the weight of the peroxyacid compound.
Additional agents which may be used to aid in giving
good bleaching performance include such things as pH adjustment
agents, bleach activators and minors such as coloring agents,
dyes and perfumes. Typical pH adjustment agents are used to ~-
alter or maintain aqueous solutions of the instant compositions ~ - -
within the 5 to 10 pH range in which peroxyacid bleaching agents ;~
are generally most useful. Depending upon the nature of other -~
optional composition ingredients, pH adjustment agents can be
either of the acid or base type. Examples of acidic pH
adjustment agents designed to compensate for the presence of
other highly alkaline materials include normally solid organic
and inorganic acids, acid mixtures and acid salts. Examples
of such acidic pH adjustment agents include citric acid,
glycolic acid, tartaric acid, gluconic acid, glutamic acid, -
sulfamic acid, sodium bisulfate, potassium bisulfate, ammonium
bisulfate and mixtures of citric acid and lauric acid. Citric
1(~79Z95
acid is preferred by virtue of its low toxicity and hardness
sequestering capability.
Optional alkaline pH adjustment agents include the
conventional alkaline buffering agents. Examples of such
buffering agents include such salts as carbonates, bicarbonates,
silicates, pyrophosphates and mixtures thereof. Sodium
bicarbonate and tetrasodium pyrophosphate are highly preferred.
Optional peroxyacid bleach activators as suggested by
the prior art include such materials as aldehydes and
ketones. Use of these materials as bleaching activators is
described more fully in U.S. Patent 3,822,114, issued July 2,
1974 to Montgomery.
A preferred dry, granular bleaching product employing
the peroxyacid bleach of the present invention involves
combining the active peroxy compound with potassium aluminum
sulfate or boric acid and the acid pyrophosphate/8-hydroxy-
quinoline subsequently coating this mixture with mineral oil
and agglomerating the coated particles with a polyethylene
glycol derivative. An alkaline pH adjustment agent is then
added to the agglomerated stabilized active as a dry mix.
Optional ingredients, if utilized in combination with
the active peroxyacid of the instant invention to form a
complete bleaching product, comprise from about 20% to about
99% weight of the total composition. Conversely, the
peroxyacid compound made using the process of the present
invention comprises from about 1~ to about 80~ of the
composition.
The bleaching compositions of the instant invention,
particularly the dry granular version, can also be added to
and made a part of conventional ~abrîc laundering detergent
compositions. Accordingly, optional materials for the instant
.
,
107929~
bleaching compositions can include such standard detergent
adjuvants as surfactants and builders. Optional surfactants
are selected from the group consisting of organic anionic,
nonionic, ampholytic, and zwitterionic surfactants and
mixtures thereof. Optional bu;lder materials include any of
the conventional organic and inorganic builder salts including
carbonates, silicates, acetates, polycarboxylates and
phosphates. If the instant stabilized bleaching compositions
are employed as part of a conventional fabric laundering --
detergent composition, the instant bleaching agent generally :-
comprises from about 1% to about 40~ by weight of such -
conventional detergent compositions. Conversely, the instant
bleaching compositions can optionally contain from about 60~ -~
to about 99~ by weight of conventional surfactant and builder
materials. Further examples of suitable surfactants and build- - -
ers are given below. --~
Water-soluble salts of the higher fatty acids, i.e.,
"soaps," are useful as the anionic surfactant herein. The
class of surfactants includes ordinary alkali metal soaps
such as the sodium, potassium, ammonium and alkanolammonium
salts of higher fatty acids containing from about 8 to about
24 carbon atoms and preferably from about 10 to about 20
carbon atoms. Soaps can be made by direct saponification
of fats and oils or by the neutralization of free fatty acids.
Particularly useful are the sodium and potassium salts of the
mixtures of fatty acids derived from coconut oil and tallow,
i.e., sodium or potassium tallow and coconut soaps.
Another class of anionic surfactants includes water-
soluble salts, particularly the alkali metal, ammonium and
alkanolammonium salts, of organic sulfuric reaction products
having in their molecular structure an alkyl group containing
_g_ : ..
~, . :
,, . , : . : .:, ,, : . . .
1079Z95
from about 8 to about 22 carbon atoms and a sulfonic acid or
sulfuric acid ester group. (Included in the term "alkyl" is
the alkyl portion of acyl groups.~ Examples of this group of
synthetic surfactants which can be used in the present detergent -
compositions are the sodium and potassium alkyl sulfates,
especially those obtained by sulfating the higher alcohols
(C8-C18 carbon atoms~ produced by reducing the glycerides of
tallow or coconut oil; and sodium and potassium alkyl benzene
sulfonates, in which the alkyl group contains from about 3 to -
about 15 carbon atoms in straight chain or branched chain
configuration, e.g., those of the type described in U.S.
Patents 2,220,099 and 2,477,383.
Other anionic surfactant compounds useful herein include
the sodium alkyl glyceryl ether sulfonates, especially those
ethers or higher alcohols derived from tallow and coconut oil;
sodium coconut oil fatty acid monoglyceride sulfonates and
sulfates; and sodium or potassium salts of alkyl phenol
ethylene oxide ether sulfate containing about 1 to about 10
units of ethylene oxide per molecule and wherein the alkyl
groups contain about 8 to about 12 carbon atoms.
Other useful anionic surfactants herein include the
water-soluble salts of esters of a-sulfonated fatty acids
containing from about 6 to 20 carbon atoms in the ester group;
water-soluble salts of 2-acyloxy-alkane-1-sulfonic acids
containing from about 2 to 9 carbon atoms in the acyl group
and from about 9 to 23 carbon atoms in the alkane moiety;
alkyl ether sulfates containing from about 10 to 20 carbon
atoms in the alkyl group and from about 1 to 30 moles of
ethylene oxide; water-soluble salts of olefin sulfonates
containing from about 12 to 24 carbon atoms; and ~-alkyloxy
alkane sulfonates containg from about 1 to 3 carbon atoms in
the alkyl group and from about 8 to 20 carbon atoms in the
--10--
1079Z~i
alkane moiety.
Preferred water-soluble anionic organic surfactants
herein include linear alkyl benzene sulfonates containing
from about 11 to 14 carbon atoms in the aIkyl group; the
tallow range alkyl sulfates; the coconut range alkyl glyceryl
sulfonates; and alkyl ether sulfates wherein the alkyl moiety
contains from about 14 to 18 carbon atoms and wherein the ;
average degree of ethoxylation varies between 1 and 6.
Specific preferred anionic surfactants for use herèin
include: sodium linear C10-C12 alkyl benzene sulfonate;
triethanolamine C10-Cl2 alkyl benzene sulfonate; sodium
tallow alkyl sulfate; sodium coconut alkyl glyceryl ether
sulfonate; and the sodium salt of a sulfated condensation
product of tallow alcohol with from about 3 to about 10 moles
of ethylene oxide. -
It is to be recognized that any of the foregoing
anionic surfactants can be used separately herein or as
mixtures.
Nonionic surfactants include the water-soluble ~
ethoxylates of C10-C20 aliphatic alcohols and C6-C12 alkyl ;
phenols. Many nonionic surfactants are especially suitable
for use as suds controlling agents in combination with anionic
surfactants of the type disclosed herein. -~
Semi-polar surfactants useful herein include water-
soluble amine oxides containing one alkyl moiety of from about
10 to 28 carbon atoms and 2 moieties selected from the group
consisting of alkyl groups and hydroxyalkyl groups containing
from 1 to about 3 carbon atoms; water-soluble phosphine oxides
containing one alkyl moiety of about 10 to 28 carbon atoms
3a and 2 moieties selected from the group consisting of alkyl
groups and hydroxyalkyl groups containing from about 1 to 3
carbon atoms; and water-soluble sulfoxides containing one alkyl
--11--
: :' , , ' ' ' ~, ~ . .
- ~ z~
moiety of from about 10 to 28 carbon atoms and a moiety selected
from the group consisting of alkyl and hydroxyalkyl moieties
of from 1 to 3 carbon atoms.
Ampholytic surfactants include derivatives of aliphatic
or aliphatic derivatives of heterocyclic secondary and tertiary .
amines in which th.e aliphatic moiety can be straight chain or
branched and wh.erein one of the aliphatic substituents contains
from about 8 to 18 carbon atoms and at least one aliphatic :.:
substituent contains an anionic water-solubilizing group. :~
Zwitterionic surfactants include derivatives of ali- .
phatic quaternary ammonium, phosphonium and sulfonium compounds
in which the aliphatic moieties can be straight or branched
chain, and wherein one of the aliphatic substituents contains .-
from about 8 to 18 carbon atoms and one contains an anionic
water-solubilizing group.
The instant granular compositions can also comp:rise
those detergency builders commonly taught for use in laundry :
compositions. Useful builders herein include any of the
conventional inorganic and organic water-soluble builder
salts, as well as various water-insoluble and so-called "seeded"
: builders. ; .
Inorganic detergency builders useful herein include,
for example, water-soluble salts of phosphates, pyrophosphates,
orthophosphates, polyphosphates, phosphonates, carbonates,
bicarbonates, borates and silicates. Specific examples of
inorganic phosphate builders include sodium and potassium
tripolyphosphates, phosph.ates, and hexametaphosphates. The
polyphosphates specifically include, for example, the sodium
and potassium salts of ethylene diphosphonic acid, the sodium
and potassium salts of ethane l-hydroxy-l,l-diphosphonic acid,
and the sodium and potassium salts of eth.ane-1,1,2-triphosphonic
.,~ . .
'' : ,
lO~g29S ~
acid. Examples of these and other phosphorus builder
compounds are disclosed in U.S. Patents 3,159,581; 3,213,030;
3,422,021; 3,422,137; 3,40Q,176 and 3,400,148.
Sodium tripolyphosphate is an especially preferred,
water-soluble inorganic builder herein.
Non-phosphorus containing sequestrants can also be
selected for use herein as detergency builders. Specific -
examples of non-phosphorus, inorganic builder ingredients
include water-soluble inorganic carbonate, bicarbonate, `
borate and silicate salts. The alkali metal, e.g., sodium
and potassium, carbonates, bicarbonates, borates (borax~ and
silicates are particularly useful herein.
Water-soluble, organic builders are also useful herein.
For example, the alkali metal, ammonium and substituted ;
ammonium polyacetates, carboxylates, polycarboxylates, -~
succinates, and polyhydroxysulfonates are useful builders in
the present compositions and processes. Specific examples of
the polyacetate and polycarboxylate builder salts include
sodium, potassium, lithium, ammonium and substituted ammonium
salts of ethylene diamine tetraacetic acid, nitrilotriacetic
acid, oxydisuccinic acid, mellitic acid, benzene polycarboxylic
acids, and citric acid. ~ -
Highly preferred non-phosphorus builder materials
(both organic and inorganic) herein include sodium carbonate,
sodium bicarbonate, sodium silicate, sodium citrate, sodium
oxydisuccinate, sodium mellitate, sodium nitrilotriacetate,
and sodium ethylenediaminetetraacetate, and mixtures thereof.
Another type of detergency-builder material useful
in the present compositions and processes comprises a water-
soluble material capable of forming a water-insoluble reaction
product with water hardness cations in combination with a
crystallization seed which is capable of providing growth
' "
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,: , :, .. . . . ..................... .
. .
107929~
sites for said reaction product.
Specific example of materials capable of forming the
water-insoluble reaction product include the water-soluble
salts of carbonates, bïcarbonates, sequicarbonates, silicates,
aluminates and oxalates. The alkali metal, especially sodium,
salts of the foregoing materials are preferred for convenience
and economy.
Another type of builder useful herein includes various ~ -
substantially water-insoluble materials which are capable of
reducing the hardness content of laundering liquors, e.g., by
ion-exchange processes. Examples of such builder materials
include the phosphorylated cloths disclosed in U.S. Patent
3,424,545, Bauman, issued January 28, 1969.
The complex aluminosilicates, i.e., zeolite-type
materials, are useful presoaking/washing adjuvants herein in
that these materials soften water, i.e., remove Ca++ hardness.
Both the naturally occurring and synthetic "zeolites", especial-
ly zeolite A and hydrated zeolite A materials, are useful for
this builder/softener purpose. A description of zeolite
materials and a method of preparation appears in Milton, U.S. -
Patent 2,882,243, issued April 14, 1959.
Composition Preparation
The bleaching compositions of the instant invention
are prepared in any conventional manner such as by admixing
ingredients, by agglomeration, by compaction or by granulation
in the case of the dry granule form. In one method for
preparing such compositions, a peroxyacid-water mixture
containing from about 50% by weight to about 80% by ~eight of
water is combined in proper proportions with any optional
components to be utilized within the bleaching granules
themselves. Such a combination of ingredients is then thorough-
ly mixed and subsequently- run through an extruder. Extrudate
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.- - .
.: `
~ \ ~
1~7929S
in the form of noodles is then fed into a spheronizer `:
(also known by the trade mark, "Marumerizer") to form
approximately spherical parti.cles from the peroxyacid- ~.
containing noodles. Th.e bleaching granules can then be dried :.:
to the appropriate water content. Upon leaving the spheronizer,
such.particles are screened to provide uniform particle size. ::
Bleaching granules prepared in this manner can then be
admixed wi.th other granules of optional bleaching or detergent
composition materials. Actual particle size of either the ~
bleach-containing granules or optional granules of additional ~-
material is not critical. If, however, compositions are to .
be realized having commercially acceptable flow properties, ~ :
certain granule size limitations are highly preferred. In
general, all granules of the instant compositions preferably.~
range in size from about lQ0 microns to 3000 microns, more ~ :
preferably from about 100 microns to 1300 microns.
Additionally, flowability is enhanced if particles of ~ .
the present invention are of approximately the same size.
Therefore, preferably the ratio of the average particle sizes
of the bleach-containing granules and optional granules of
other materials varies between 0.5:1 and 2.0:1. .. ~
Bleaching compositions of the present invention are . .
utilized by dissolving them in water in an amount sufficient ~ .
to provide from about 1.0 ppm to 100 ppm available oxygen in ..
solution. Generally, this amounts to about 0.01% to 0.2% by
weight of composition in solution. Fabrics to be bleached
are then contacted with such. aqueous bleaching solutions.
me bleaching compositions of the instant invention . .
are illustrated by the following examples:
EXAMPLE I .~. :
An example of the process of the present invention
is as follows:
-15-
.-` 10~7gZ95 ~.
An open beaker is charged with 13.3 grams of hydrogen
peroxide C100%1 and 28.1 grams of water. This solution is
cooled to below 10C and 12a grams of sulfuric acid (100%1
are added dropwise. This premix is warmed to 35C and 30
grams of powdered dodecanedioic acid are added with stirring.
The reaction mixture is maintained at a temperature of 35C.
Samples are taken at various times and treated as follows: ~-
the samples are quenched immediately in an excess of ice
water; the product crystals formed are washed with water
and dried; and the product is analyzed by conventional
iodometric techniques for available oxygen. It is found that
conversion from the dibasic acid to the diperoxyacid is
quickly achieved using the above conditions.
EXAMPLE II
The process as described in Example I is repeated
using 8.35 grams of hydrogen peroxide, 14.1 grams of water,
80 grams of sulfuric acid and 20 grams of a powdered form
of the acid
O O
Il 11
HO - C - ~CH2~11 - C OH
The diperoxyacid is formed quickly.
EXAMPLE III
The process of Example I is repeated using 7.9
grams of hydrogen peroxide, 13 grams of water, 80 grams of
sulfuric acid and 20 grams of the powdered acid
O O
Il 11
HO C (CH2~12 C OH
The diperoxyacid is formed quickly.
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