You are on page 1of 7

US 20060281937Al

(19) United States
(12) Patent Application Publication (10) Pub. No.: US 2006/0281937 A1
Heider et al. (43) Pub. Date: Dec. 14, 2006

(54) STEARATE COMPOSITION AND METHOD (60) Provisional application No. 60/490,596, ?led on Jul.
28, 2003.
(76) Inventors: Todd P. Heider, Imperial, MO (US);
Steven M. Wolfgang, Reston, VA (U S); Publication Classi?cation
Scot R. Randle, St. Louis, MO (US)
(51) Int. Cl.
Correspondence Address: C07C 51/43 (2006.01)
Mallinckrodt Inc. (52) US. Cl. ............................................................ .. 554/195
675 McDonnell Boulevard
PO Box 5840 (57) ABSTRACT
St. Louis, MO 63134 (US) An improved alkaline earth metal stearate composition is
disclosed and is prepared by reacting a fatty acid component
(21) Appl. No.: 11/154,849
including stearic acid and palmitic acid With an alkali
Filed: Jun. 16, 2005 hydroxide to form an alkaline soap. An aqueous metal salt
(22) solution is then added to the soap, and pH adjusted to less
Related US. Application Data than about pH 8 to form the improved alkaline earth metal
stearate. The improved alkaline earth metal stearate provides
(63) Continuation-in-part of application No. PCT/US04/ a substantially pure amount of the dihydrate form of the
24485, ?led on Jul. 28, 2004. stearate.
US 2006/0281937 A1 Dec. 14, 2006

STEARATE COMPOSITION AND METHOD obtain pure dihydrate, or even signi?cant amounts of dihy
drate. The lack of consistency in commercial fatty acid
REFERENCES TO RELATED APPLICATIONS compositions make controlling the content of dihydrate in
the ?nished product challenging. The dihydrate is not an
[0001] This application is a continuation-in-part of PCT/ intermediate substance in the formation of the trihydrate
US2004/024485, ?led Jul. 28, 2004, Which designated the from the anhydrous form When it Was exposed to high
United States and claims priority to US. provisional appli humidity, and is only crystallized from solution under cer
cation No. 60/490,596, ?led Jul. 28, 2003. tain circumstances.
[0007] Further, currently available magnesium stearate
BACKGROUND OF INVENTION compositions have the potential to adversely affect pharma
[0002] This invention relates to the industrial manufacture cological activity by providing a Water repellant barrier to
of alkaline earth metal stearate compositions useful as dissolution of drugs, and can have a major in?uence on
industrial lubricants for uses including metal forming and bioavailability, particularly of sustained release drugs.
tablet formulation of pharmaceutical preparations. More [0008] In order for the pharmaceutical industry to gauge
particularly, this invention relates to a process for preparing the potential bene?ts of the dihydrate form for the purpose
magnesium stearate lubricant exhibiting improved proper of creating neW formulations based on these ?ndings, pure
ties in lubrication and dissolution of pharmaceutical prepa or at least Well-de?ned compositions containing dihydrate
rations in tablet form. material must ultimately become commercially available.
[0003] Numerous patents disclose the utility of stearates as [0009] Commercially available magnesium stearate is
lubricants or poWder ?oW enhancers. US. Pat. Nos. 6,437, actually a mixture of magnesium stearate and palmitate, and
000, 5,032,632, 5,952,004, 5,447,729, 4,800,082, 4,777,080 the hydration and degree of crystallinity vary signi?cantly
and US. Published Application 2002/0052411 provide typi depending upon the manufacturing process, as Well as from
cal disclosures of such utility. batch to batch depending on the starting materials. While
high-purity forms of magnesium stearate dihydrate or mag
[0004] The use of magnesium stearate as a pharmaceutical nesium palmitate dihydrate have been prepared and charac
tableting lubricant is Well knoWn in the art. According to teriZed in the laboratory, there are no commercially viable
USP/NF (2004), magnesium stearate is described as a sub methods available for the preparation of the preferred dihy
stance containing at least 40% stearic acid, 90% as the sum drate form.
of stearic acid and palmitic acid, and not more than 6.0%
[0010] Improvements and ef?ciencies in the industrial
Water. Magnesium stearate commonly used in pharmaceu
preparation of stearate salts have been the subject of con
tical applications is a mixture of magnesium stearate and
siderable research. As the number and use of medications,
magnesium palmitate, since sources used to derive magne
particularly in tablet form, expands, so to does the demand
sium stearate include talloW, palm oil, and soybean oil, all of for ingredients employed in pharmaceutical tablet formation
Which are glyceryl esters of C16 and C18 fatty acids. More as Well as in industrial operations. One such industrial
over, the state of magnesium stearate may be amorphous, or
application is metalworking that has also increased demand
exhibit any of the folloWing crystalline formsianhydrous, for reasonable priced lubricants of the stearate class, as is
monohydrate, dihydrate, and trihydrate. The USP/NF
found in US. Pat. No. 5,277,832.
description of the composition and attributes of magnesium
stearate does not account for functionality differences of the [0011] Another attempt to gain ef?ciency and an improved
various crystalline forms. Further, the Water content of up to product is disclosed in US. Pat. No. 5,175,322. This patent
6.0% alloWs for products containing many possible combi discloses a continuous process for manufacturing alkaline
nations of hydrated forms to meet the requirements in the earth metal stearate soaps by the double decomposition
compendial monograph. method Wherein a stream of an alkaline earth metal soap and
an inorganic metal salt is dropped on a moving impeller of
[0005] Pharmaceutical manufacturers and researchers a mixer thereby instantaneously mixing the reactant together
have found that of the three polymorphic hydrates (mono-, folloWed by rapid discharge from the reactor of the neWly
di- and tri-), the dihydrate form is preferred as it provides formed stearate salt. This process is purported to provide a
superior lubricating properties. It is also knoWn that the product free of unreacted starting materials and unWanted
content of Water and the resulting crystal forms contribute to by-products. An improved double decomposition reaction
functionality of magnesium stearate. Magnesium stearate Was disclosed in US. Pat. No. 5,434,277 Wherein it is
compositions that contain some dihydrate are perceived to disclosed that such reactions do not provide high purity
have advantages in the formulation and manufacture of solid products because of the presence of unreacted starting
dosage forms. It has been reported that improvements in materials present in the product. The solution to this problem
disintegration, dissolution, crush strength and extrusion according to this disclosure is to provide alternated basi?
force are related speci?cally to the presence of dihydrate as cation-acidi?cation of the reaction mixture. The effective
opposed to other hydrated forms of magnesium stearate. ness of the alternate treatment of the reaction mixture Was
Dihydrate has been reported to have the best anti-caking shoWn by DSC analysis of the product indicating the dis
properties. appearance of stearic acid starting material after alternative
[0006] HoWever, the prior art has failed to describe a treatment. None of the prior disclosures mention the rel
method to manufacture the dihydrate from a mixed fatty acid evance of stearic acid/palmitic acid composition impacting
composition that typi?es commercial sources in terms of its hydration nor any means to control hydration of precipitated
stearic acid/palmitic acid content, nor a method for prepar stearates in aqueous media.
ing it. There is no description in the prior art to suggest that [0012] A publication entitled “The Magnesium Stearate
commercial fatty acids have the correct composition to Problem” originally presented as a paper in 1992 and then
US 2006/0281937 A1 Dec. 14, 2006

published in Manufacturing Chemist, December 1993 dis Wherein a substantial portion of the stearate is in the dihy
closes a study of the variations in lubricant properties of drate form. Methods of making metallic salts of fatty acids
products from various industrial batches of stearate that has are Well knoWn in the art. The “double decomposition”
been observed in the industry. The observed variations Were method involves a tWo-step process. First, the fatty acid is
reported by K. J. Stelfens and J. Koglin in an attempt to reacted With at least one base in a basic aqueous solution,
determine the unexplained cause of performance variation of typically at least one alkali hydroxide to form an alkaline
industrial production batches of stearate salt that seemed soap. Second, at least one aqueous metallic salt solution is
identical based on the manufacturers reported attributes. added to the soap to form metallic salts of the corresponding
Signi?cant variations Were observed among the commercial fatty acid.
sources With respect to lubrication and tablet properties.
[0021] Conventional pharmaceutical preparation of alka
[0013] The Writers classi?ed commercial grades of mag line earth metal stearates, for example magnesium stearate
nesium stearate into six types distinguished by differences in and calcium stearate, typically utiliZe this method. The
their hydration and crystallinity. It Was determined that stearic acid reacts With an alkali hydroxide, for example
crystalline magnesium stearate containing “predominately NaOH, to form the sodium soap, Which then reacts With an
dihydrate form” Was clearly superior When used as lubricant alkaline earth metal salt, for example magnesium chloride,
in a model formulation. Unfortunately, no method of manu as shoWn beloW:
facturing the pure dihydrate phase has been described in the
literature, With the exception of synthesis from relatively
pure stearic acid, Which is cost prohibitive.
[0014] It is therefore desirable to provide an alkaline earth
metal stearate composition and related method of production [0022] Stearate compositions produced by this method
that result in consistent production of the dihydrate form of exhibit great variation in quality and properties. It is knoWn
the alkaline earth metal stearate. that commercially available stearic acid typically contains
palmitic acid also. While pure stearic acid does have limited
SUMMARY OF INVENTION availability, the puri?cation is not feasible on a industrial
scale.
[0015] An aspect of the present invention is to provide an
improved alkaline earth metal stearate composition com [0023] It has noW been determined, hoWever, that this
prised of the reaction product of at least one fatty acid in a impurity (palmitic acid) can lead to the formation of an
basic solution With at least one alkaline earth metal sulfate. improved stearate composition. By manipulating the com
The fatty acid is comprised of at least about 80% by Weight ponents of the stearic acid starting material, more speci?
stearic acid and at least about 5% by Weight palmitic acid. cally the ratio of stearic acid to palmitic acid, a signi?cant
amount of the dihydrate form of the stearate product can be
[0016] Another aspect of the present invention is to pro formed. The dihydrate form of the stearate provides a
vide a method for preparing the improved alkaline earth product Which is substantially crystalline, With substantial
metal stearate composition. At least one fatty acid comprised platelet formation. The dehydrate form is thought to be
of at least about 80% by Weight stearic acid and at least responsible for the improved lubricating properties and
about 5% by Weight palmitic acid is added to a basic decreased interference With bioavailability observed With
aqueous solution. At least one alkaline earth metal sulfate is the stearate dihydrate When compared With stearates of
added, and the at least one alkaline earth metal sulfate reacts similar properties excepting for their hydration.
With the at least one fatty acid to form the improved alkaline
earth metal stearate composition. [0024] In the present invention it has been determined that
a fatty acid component of at least about 80% by Weight
[0017] In yet another aspect of the present invention there stearic acid and at least about 5% by Weight palmitic acid,
is provided an improved alkaline earth metal stearate com With 88% by Weight stearic acid to about 10% by Weight
position comprised of at least about 40% alkaline earth palmitic acid being preferred; 90% by Weight stearic acid to
metal stearate dihydrate. 8% by Weight palmitic acid being more preferred; and about
[0018] In yet a further aspect of the present invention there 93% by Weight stearic acid to about 5% by Weight palmitic
is provided a method for preparing an alkaline earth metal acid being optimal.
stearate composition. The method comprises providing a [0025] In an alternative embodiment, in addition to using
basic aqueous solution and incorporating at least one fatty preferred compositions of stearic/palmitic acids, the Water
acid into the basic aqueous solution. The fatty acid is content of the stearic/palmitic acids is de?ned. In this
comprised of stearic acid and palmitic acid. embodiment, the composition disclosed is comprised of
[0019] At least one alkaline earth metal sulfate is added to magnesium stearate palmitate dihydrate having a stearate/
form a slurry, and the slurry pH is adjusted to less than about palmitate ratio of at least 10:1 and a total Water content of
pH 8. The slurry is then subjected to solid-liquid separation less than about 6%. Of that 6% Water, preferably 15-100%
via vacuum ?ltration and resulting Wet cake is ?ash dried to of the total Water content is crystalline Water dihydrate, With
form the improved alkaline earth metal stearate composi less than about 10% of the total Water content being free
tion. Water, and the remainder of the Water content being mono
hydrate. The fatty acid stream used in this alternative
BRIEF DESCRIPTION OF DRAWINGS embodiment contains the sum of stearate and palmitate no
less than 98% of the total acid content. The Water content
[0020] There is provided an improved alkaline earth metal and hydration state of the ?nal product vary as the ratio of
stearate composition and related method of preparation, stearic acid/palmitic acid, pH and conditions of drying are
US 2006/0281937 A1 Dec. 14, 2006

varied. The desired dihydrate is most likely to form in trative reaction equation beloW utiliZes magnesium sulfate
alkaline solution When the ratio of stearic acid/palmitic acid as the alkaline earth metal sulfate.
is >10, or at a lesser ratio When the pH is closer to neutral
and When the drying temperature does not exceed 60° C. Mg(C17H35COO)2.xH2O+Na2SO4+6H2O (5)
[0026] The composition disclosed in this alternative [0032] The alkaline earth metal sulfate is added in slight
embodiment exhibits bene?cial functionalities including excess to ensure that all sodium stearate reacts to form the
improving poWder ?oW characteristics, reducing ejection alkaline earth metal stearate. The pH after this step is
force/compression force ratio, and minimizing any retarda typically about 6.0-6.7. It is noted that the soap solution may
tion of disintegration and dissolution rates of hydrophobic, be produced by any conventional method, as are Well knoWn
or poorly Water soluble drugs such as dilantin, moda?nil, in the art.
Zolpidem and alike, Which are frequently observed When [0033] The soluble salts are removed from the product by
conventional magnesium stearate Was used as the lubricant adding Water to the slurry, mixing and then separating and
in making the tablets. draining off the Water. The pH after this step is typically
[0027] According to these ?rst tWo embodiments of the about 8.0-8.5.
present invention, the fatty acid component is dispersed into [0034] The pH of the alkaline earth metal stearate slurry is
a basic aqueous solution, Whereby the fatty acid component then adjusted With an acid. Suitable acids include but are not
reacts With the base to form a soap. Optionally, the basic limited to organic acids such as sulfuric acid, hydrochloric
aqueous solution may be heated prior to incorporating the acid, nitric acid and mixtures thereof. The pH is preferably
fatty acid component to help to prevent the fatty acid adjusted to beloW about pH 8; With a pH of beloW 7 being
component from congealing. The alkaline earth metal salt, more preferred; and a pH of about 6.3 to about 6.4 being
typically magnesium sulfate or calcium sulfate, is then most preferred, although signi?cant formation of the dihy
added and the pH is adjusted to provide an alkaline envi drate form has been accomplished at loWer pH’s, for
ronment to raise the assay of the product by precipitation of example at pH 5. The pH may be adjusted before or after the
any excess Mg as MgO. precipitation of the stearate. In an illustrative embodiment,
the pH adjustment is made immediately before feeding to
[0028] In yet another alternative embodiment, a substan the ?ash drying system.
tially pure magnesium stearate dihydrate is attained by
controlling the pH during the precipitation step. As is [0035] In an illustrative example utiliZing magnesium
outlined above, the conventional method for producing sulfate, Wet cakes formed at pH of 6.3-6.4 Were substantially
magnesium stearate comprises the reaction of stearic acid pure magnesium stearate dihydrate, at least about 95% or
With an alkali hydroxide to form a metal soap, Which then better, With no other hydrated forms present, as analyZed
reacts With an alkaline earth metal salt to form the magne using Thermogravimetric Analysis. In one embodiment, the
sium stearate. In the conventional reaction, the formation of liquid or slurry remaining after Wet cake formation is
the hydrated magnesium soaps is a consequence of the recovered for use as a component in the basic aqueous
aqueous precipitation medium. The most common hydrated solution of subsequent dihydrate formation.
form obtained When the resulting solution is alkaline is the
monohydrate form. [0036] There Was also a signi?cant amount of dihydrate
present When the pH Was adjusted to 8.0 before drying. The
[0029] It has been determined that if the pH of the pre dihydrate Was approximately 70% With the remainder being
cipitation medium is less alkaline, or When the solution is monohydrate form.
adjusted to a pH of less than about 8, either during or after
precipitation, there is a greater tendency to obtain the [0037] It is believed that signi?cant amounts of dihydrate
hydrated form, magnesium stearate dihydrate. In this are formed When the pH of the aqueous magnesium stearate
embodiment, the fatty acid starting material can be any slurry is loWer than 8.5 before drying. At a pH above 8.5, the
combination of stearic and palmitic acid totaling at least amount of dihydrate decreases rapidly until there is no
90%. This alloWs the production of the dihydrate form from dihydrate formed When the pH of the aqueous magnesium
any commercially available fatty acid mixtures, Which are stearate slurry is adjusted to a pH of 9.0 or higher.
typically only about 40% stearic acid, With at least about [0038] The magnesium stearate is typically ?ash dried at
90% total stearic and palmitic acid. about 50 to about 90° C. With about 60 to about 65° C. being
preferred. The product tends to dehydrate slightly upon
[0030] The fatty acid is reacted With sodium hydroxide in drying, but still contains greater than about 80% dihydrate
Water at a temperature of about 75° C., forming a soluble
form With the remainder being the anhydrous crystal of the
sodium stearate/sodium palmitate mixture Which is be
dihydrate. An illustrative drying system consists of a rotary
referred to as “soap solution.” The fatty acid and sodium
hydroxide are reacted at an approximately 1:1 molar ratio
vacuum ?lter (solid-liquid separation), hammer mill, natural
and sodium hydroxide added to produce a soap solution
gas-fueled fumace, and a pneumatic conveying system,
Which is slightly alkaline. Any combination of stearic and
although the product may be dried and processed by any
conventional method. Other suitable types of drying include
palmitic acids can be used to form the relatively pure
spray drying, tray drying, and ?uid bed drying at the 50-90°
dihydrate form of magnesium stearate.
C. range to retain the dihydrate that Was formed during pH
adjustment of the magnesium stearate slurry.
[0031] An aqueous alkaline earth metal sulfate solution is [0039] The folloWing examples are given for illustrative
then added to the soap solution, Whereby insoluble alkaline purposes only and are not intended to limit the scope of the
earth metal stearate is precipitated. The non-limiting illus present invention in any Way.
US 2006/0281937 A1 Dec. 14, 2006

EXAMPLES stearate) as a result of 2 pseudopolymorphs that are each
Example 1 derived from unique hydrates.
[0040] A magnesium stearate composition containing a [0047] 3. X-ray diffraction shoWed crystallinity (not amor
variable ratio of discrete monohydrate and dihydrate poly phous), and exhibited a characteristic XRD pattern indicat
morphs is manufactured from a “soap solution” via precipi ing the dihydrate form is present.
tation, as is Well knoWn in the art. The salt of this illustrative [0048] The product had regular or irregular (e.g. frag
example is formed by mixing of at least one fatty acid and mented) platelet morphology. Other features of the manu
at least one strong base, NaOH and a magnesium salt, facturing process that are considered relevant to the manu
MgSO4. In the present invention, the soap solution is facture of magnesium stearate are obvious to those skilled in
produced from a fatty acid mixture of suitable stearic/ the art.
palmitic acid composition to obtain an appreciable amount
of the dihydrate form of the resulting stearate. Addition of Example 2
the alkaline earth metal salt to an alkaline “soap solution”
results in the precipitation of magnesium stearate containing [0049] A magnesium stearate composition is prepared
the dihydrate phase. The precipitate is separated from the according to the method of Example 1 utiliZing fatty acid
liquor, and dried to a Water content of 3.5-6.0%, predomi having a stearic/palmitic acid ratio of at least about 10:1 and
nately Water of hydration. A ?ne-particulate solid is a total Water content of less than about 6%. Of that 6% Water,
obtained. The product is designed for use as a pharmaceu preferably 15-100% of the total Water content is crystalline
tical lubricant/mold release agent, but can be used for other Water dihydrate, With less than about 10% of the total Water
applications, as is knoWn in the art. content being free Water, and the remainder of the Water
content being monohydrate. The fatty acid stream used in
[0041] The folloWing is an illustrative example of an this alternative embodiment contains the sum of stearate and
industrial manufacturing process for a product containing palmitate no less than 98% of the total acid content. The pH
the desired magnesium stearate dihydrate and is not intended adjustment is made to render the reaction mixture substan
to limit the present invention to the production of magne tially neutral. The product is dried at a temperature at or
sium stearate/palmitate for pharmaceutical uses: beloW 60° C. to remove most of the bulk Water resulting in
[0042] An aqueous solution, either Water or a heel from a a ?ne, crystalline poWder containing the dihydrate phase as
previous batch Was heated to a temperature at Which the fatty evidenced by TGA/DSC.
acid did not congeal When introduced to the aqueous solu
tion, as is Well knoWn. A 50% sodium hydroxide solution Example 3
Was added in at least a 1:1 molar ratio to the fatty acid, so [0050] A magnesium sulfate solution is prepared by dis
that substantially all the fatty acid constituents Were con solving 98 grams of magnesium sulfate heptahydrate in 643
verted to the sodium soap. The fatty acid component Was mL of Water. The mixture is stirred at 80° C. until the salt is
then added until the solution Was slightly alkaline to phe dissolved. In a separate vessel add 34 mL of 50% (W/W)
nolphthalein indicator. In this illustrative example, a fatty NaOH to 1.13 liters of Water and heat to 90° C. An alkaline
acid composition of about 93% by Weight stearic acid to sodium stearate (soap) is made by adding 181 grams of fatty
about 5% by Weight palmitic acid Was used. acid containing 93% stearic acid and 5% palmitic acid to the
[0043] A solution of magnesium sulfate Was then added, NaOH solution maintaining the temperature at 90° C. While
Without agitation, in an amount to substantially precipitate stirring. 681 mL of Water is added to the soap solution,
the sodium soap, thereby forming the magnesium stearate/ loWering its temperature to 75° C. The magnesium sulfate
palmitate. The reaction mixture Was then mixed to create a solution is added to the soap solution and stirred to assure
homogeneous mixture and insure reaction With the magne complete reaction. Once the precipitation is complete the
sium sulfate, typically about 20 minutes. The reaction mix batch is adjusted to a pH of 9.0 using 50% NaOH. The
ture remained heated throughout this and the remaining resulting solids are Washed With Water to remove sodium
steps to prevent any solidi?cation of the reaction mixture, sulfate byproduct. The solids are dried at 60° C. The product
thereby providing ease of handling. The pH Was then contains a combination of the monohydrate and dihydrate
adjusted With sodium hydroxide to precipitate any excess forms of magnesium stearate palmitate.
magnesium as MgO. An illustrative pH range is from about
9.0 to about 9.5. A solid-liquid separation Was performed, Example 4
and the resulting solid product Was dried, and deagglomer [0051] A soap solution Was formed by reacting a fatty acid
ated by suitable conventional methods. These steps and (a mixture of about 65% Stearic and about 35% Palmitic and
reaction conditions are Well knoWn to those skilled in the art.
small percentage of other fatty acids) (181 g) With sodium
[0044] This resulting product Was characterized as con hydroxide in Water (34 ml of 50% Wt/Wt NaOH added to
taining a mixture of magnesium stearate and magnesium 1.13 liters of Water) at 90° C., forming a soluble sodium
palmitate as mixed hydrates as folloWs: stearate soap solution. The resulting soap solution is slightly
alkaline so that 5 mL of the slurry dissolved in acetone
[0045] 1. The product had a loss on drying of 3.5-6.0% solution, Water and phenolphthalein indicator requires 0.1
indicating a signi?cant amount of the dihydrate form is 0.3 mL of 0.1 N HCl to titrate to the endpoint. Aqueous
present. TGA indicates 2 Water loss events, one at about 60°
magnesium sulfate solution prepared by dissolving 98 grams
C. and one at about 90° C., corresponding to the dihydrate of magnesium sulfate heptahydrate in 643 mL of Water. The
and monohydrate forms respectively. magnesium sulfate solution Was added to the soap solution
[0046] 2. DSC analysis shoWed 2 endothermic transitions and 191 g insoluble magnesium stearate (Weight as the
betWeen 100°-135° C. (ca. 118° C. and 128° C. for Mg monohydrate) Was precipitated. The magnesium sulfate Was
US 2006/0281937 A1 Dec. 14, 2006

added in slight excess to ensure that all sodium stearate [0064] Having described the invention in detail, those
reacts to form magnesium stearate. The pH after this step skilled in the art Will appreciate that modi?cations may be
Was 6.2-6.8. The pH Was adjusted to a range of 9.0 to 9.5 by made of the invention Without departing from its’ spirit and
adding 50% Wt/Wt NaOH in Water. The soluble salts Were scope. Therefore, it is not intended that the scope of the
removed by Washing the product With city Water (3400 ml.) invention be limited to the speci?c embodiments described.
The pH after this step Was 8.5. Immediately before feeding Rather, it is intended that the appended claims and their
the magnesium stearate slurry into a ?ash drying system, the equivalents determine the scope of the invention.
pH of the slurry Was adjusted by adding sulfuric acid until
a pH of 6.3 Was attained. The resulting Wet cakes formed at 1. An improved alkaline earth metal stearate composition
pH of 6.3 Were substantially pure magnesium stearate dihy comprised of at least about 40% earth metal stearate dihy
drate, greater than 90% purity, With no other hydrated forms drate.
present When analyZed using thermogravimetric analysis. 2. The composition of claim 1 Wherein the alkaline earth
The magnesium stearate Was ?ash dried at With a target metal stearate composition is comprised of at least about
temperature of 71° C., resulting in slight dehydration of the 70% alkaline earth metal stearate dihydrate.
product, but greater than 80% dihydrate form With the 3. The composition of claim 1 Wherein the alkaline earth
remainder being the anhydrous crystal of the dihydrate. metal stearate composition is comprised of at least about
99% alkaline earth metal stearate dihydrate.
[0052] The drying system consisted of a rotary vacuum 4. The composition of claim 1 Wherein the alkaline earth
?lter (solid-liquid separation), hammer mill, natural gas metal is selected from the group consisting of magnesium
fueled furnace, and a pneumatic conveying system. The and calcium.
?ash drying system has a residence time of less than 30 5. An improved magnesium stearate composition com
seconds and a typical inlet temperature of 150 to 2600 C. The prised of at least about 40% magnesium stearate dihydrate.
hammer mill contains 12 hammers and rotates at 1800 rpm 6. The composition of claim 5 Wherein the magnesium
and acts mainly to deagglomerate the Wet cake to facilitate stearate composition is comprised of at least about 70%
drying. magnesium stearate dihydrate.
7. The composition of claim 5 Wherein the magnesium
Example 5 stearate composition is comprised of at least about 99%
[0053] A magnesium stearate composition Was made magnesium stearate dihydrate.
according to Example 4, adjusting the pH to 5.0. The 8. A method for preparing an alkaline earth metal stearate
resulting composition Was greater than 90% magnesium composition comprising:
stearate dihydrate, With no other hydrated forms present
When analyZed using thermogravimetric analysis. providing a basic aqueous solution;
incorporating at least one fatty acid, the fatty acid includ
Example 6 ing at least about 90% total stearic acid and palmitic
[0054] Three magnesium stearate compositions Were acid, into the basic aqueous solution;
made according to Example 4, adjusting the pH to 6.3, 7.3 adding at least one alkaline earth metal sulfate, Whereby
and 8.0. The resulting compositions Were characterized via the alkaline earth metal stearate precipitates to form a
x-ray poWder diffraction. A Siemens D500 X-ray Dilfracto slurry of the alkaline earth metal stearate composition;
meter utiliZing a Long Fine Focus X-ray Tube (Type: FL Cu and
4KE) and a di?fracted beam monochromator mounted in
front of a scintillation detector. The instrument Was inter adjusting the pH of the slurry to less than about pH 8.
faced With an IBM-compatible computer for data acquisition 9. The method of claim 8 Wherein the basic aqueous
and analysis using Materials Data, Inc. softWare including solution comprises Water and NaOH.
DataScan and Jade. Each sample Was uniformly crushed 10. The method of claim 8 Wherein the pH of the slurry
(not ground) With a spatula edge, and dispersed on a quartz, is adjusted to less than about pH 7.
Zero-background holder. 11. The method of claim 8 Wherein the pH of the slurry is
adjusted to a pH of about 6.3 to a pH of about 6.4.
[0055] Experimental Parameters: 12. The method of claim 8 Wherein the pH of the slurry
[0056] Scan rangei2.0 to 40.0 deg 2-theta is adjusted to a pH of about 5.0.
13. The method of claim 8 Wherein the pH is adjusted With
[0057] Display rangei2.0 to 40.0 deg 2-theta an organic acid selected from the group consisting of sul
[0058] Step siZe40.02 deg 2-theta furic acid, hydrochloric acid, nitric acid and mixtures
thereof.
[0059] Scan time per stepi1.0 seconds 14. The method of claim 8 Wherein the pH is adjusted
[0060] Radiation sourceicopper KO. (1.5406 A) before the alkaline earth metal stearate precipitates.
15. The method of claim 8 Wherein the pH is adjusted
[0061] X-ray tube poWer*40 kV/30 mA after the alkaline earth metal stearate precipitates.
16. The method of claim 8 further comprising performing
[0062] The pattern obtained for the composition adjusted a liquid-solid separation to remove the alkaline earth metal
to pH 6.3 Was consistent With substantially pure dihydrate stearate composition from the slurry.
form.
17. The method of claim 16 further comprising recovering
[0063] The pattern obtained for the compositions adjusted the slurry for use in a subsequent preparation of alkaline
to pH 7.3 and 8.0 Were consistent With a mixture of earth metal stearate composition, Wherein the recovered
monohydrate, dihydrate and trihydrate phases. slurry is added to the basic aqueous solution.
US 2006/0281937 A1 Dec. 14, 2006

18. The method of claim 8 wherein the alkaline earth 21. The method of claim 19 Wherein the pH is adjusted
metal is selected from the group consisting of magnesium With an organic acid selected from the group consisting of
and calcium. sulfuric acid, hydrochloric acid, nitric acid and mixtures
19. A method for preparing a magnesium stearate com thereof.
position comprising: 22. The method of claim 19 Wherein the pH is adjusted to
less than about 7.
providing a basic aqueous solution; 23. The method of claim 19 Wherein the pH is adjusted to
heating the basic aqueous solution; a pH of about 6.3 to about 6.4.
24. The method of claim 19 Wherein the pH of the slurry
incorporating at least one fatty acid, the fatty acid includ
is adjusted to a pH of about 5.0.
ing at least about 90% total stearic acid and palmitic
25. The method of claim 19 Wherein the pH is adjusted
acid, into the basic aqueous solution, continuing heat before the magnesium stearate composition precipitates.
ing the basic aqueous solution and the at least one fatty
26. The method of claim 19 Wherein the pH is adjusted
acid until the at least one fatty acid is dispersed Within
after the magnesium stearate composition precipitates.
the basic aqueous solution; 27. The method of claim 19 further comprising perform
adding a solution of magnesium sulfate, Whereby the ing a liquid solid separation to recover the magnesium
magnesium sulfate reacts With the at least one fatty acid stearate composition from the slurry.
to form the magnesium stearate composition; and 28. The method of claim 27 further comprising recovering
the slurry for use in a subsequent preparation of alkaline
adjusting the pH of the resulting solution to less than a pH
earth metal stearate composition, Wherein the recovered
of about 8.
slurry is added to the basic aqueous solution.
20. The method of claim 19 Wherein the basic aqueous
solution comprises Water and NaOH. * * * * *