DE1900171A1 - Process for the production of organotin compounds - Google Patents

Description

Description of the patent application of

Billiton- M&T Chemische Industrie N.V ", The Hague / Netherlands

_x concerning

■ Λ-

Process for the preparation of organotin compounds

Priority: -2, January 1968 -'tr.St / A.

The invention relates to a ncsues method of manufacture of organotin compounds * ß the invention relates in particular on a new process for the production of these compounds »which is characterized by the ease of the Production of desired compounds in high purity from -; /

909837/1518

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According to the invention there is thus a method of manufacture proposed by dioctyltin diearboxylates, which thereby it is carried out that one essentially stoichiometric amounts Dioctyltin oxide and dicarboxylic acid or dicarboxylic acid anhydride in the presence of an inert aliphatic hydrocarbon solvent reacted as a reaction medium, whereby dioctyltin dicarboxylate is formed; that one called daa After the reaction has ended, the reaction medium is cooled, whereby said dioctyltin dicarboxylate precipitates; that one called daa recovered crystallized dioctyltin dicarboxylate as product; and that during this extraction one could inert aliphatic © hydrocarbon solvent in liquid Phase holds.

The dicarboxylic acids that are used in the process according to the invention

can be used are, for example, "Alkylenedicarboxylic acids, such as e.g., adipic acid or succinic acid, or alkenylenedicarboxylic acids, such as maleic acid. The corresponding acid anhydrides can also be used, namely succinic anhydride, Adipic anhydride, maleic anhydride, etc.

The preferred maleic anhydride used in accordance with the invention is the commercially available maleic anhydride. Optionally, maleic acid can be used instead of

909837/151 *

BATH ORIGINAL

"3 -.
and used as the equivalent of maleic anhydride «

The dioctyltin oxide which can be used according to the invention can be di-n-voctyltin oxide or di-i-octyltin oxide or di-2-ethylhexyltin oxide etc. The preferred reaction participant according to the method of the invention is di-noetyltin oxide. This oxide can typically be obtained in a purity of at least $ 95 and with a water content of less than \% .

The inert aliphatic hydrocarbon solvents which can be used as a reaction medium according to the invention are, for example, those having 5-16 and preferably 6-8 and, for example, 7 carbon atoms in the molecule. Typically Weiee dxese straight or verzvreigtkettigen inert aliphatic solvent can be alkanes such as hexane, -1 · Hept & n, octane, nonane, decane, etc. Cycloaliphatic solvent, wis for example, cyclohexane _f cyclohexene, methylcyclohexane, Äthylcyclohexan, 1,2-dimethylcyclohexane, etc ., can also be used. According to the invention, saturated aliphatic straight-chain hydrocarbon solvents are preferably used * The inert aliphatic hollow hydrogen solvent is preferably one with a boiling point of at least about 65 G (and preferably above the melting point of the anhydride used) and less than 150 ⁰ C. Bas

909837/1518 '

'SAD ORIGINAL *

190017t

.... 4 "

preferred solvent has a boiling point of about 8O ⁰ C, preferably about 10O ⁰ C and is preferably heptane. Various isomers or mixtures of these solvents can be used «Commercially available mixtures, such as commercial heptane (such as a commercial heptane with a boiling point of about 99 ° ^e )» and commercial isoparaffin mixtures with a boiling range of 126-143 ° ^C for example Isopar B solvents) can be used. Inert aliphatic hydrocarbon solvents containing minor amounts of other solvents can also be used, but to obtain the maximum benefit from the process of the invention it is preferred to use substantially pure inert aliphatic hydrocarbon solvent, preferably in anhydrous form. If aromatic solvents, such as benzene, toluene, etc., are present, then they should preferably be present in an amount of less than 5% and in particular less than i £.

In carrying out the method of the invention A preferred embodiment is 70-120 parts, preferably 100 parts, inert aliphatic hydrocarbon solvent, preferably heptane, placed in a reaction vessel. 27.2-27.8 parts, preferably 27.6 parts, maleic acid

,,, -.-- 909837-M51 *

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anhydride (or an equivalent molar amount of other dicarboxylic acids or anhydrides) are then added to the reaction vessel. The ratio of solvent to dicarboxylic acid or anhydride can be such that the reaction product is soluble in the solvent at elevated temperatures and crystallization occurs at the recovery temperatures. The preferred ratio of solvent to maleic anhydride is maintained at a weight ratio of 2.5: 1 to 5 * 1 »preferably 2.7: 1, as the correct solubility of the product in the solvent at elevated temperatures and maximum crystallization at the Recovery temperatures results. This ensures that the desired ratio of solvent to product O _T 55: 1 to 2: 1 _f for example 0.6: 1 is »

The reaction mixture can be heated to a temperature above the melting point of the acid or the anhydride. If the acid is used, the system can be heated to reflux to separate the water formed. The reaction mixture is preferably heated above the melting point of the anhydride. In the case of maleic anhydride, the temperature is 60-7O ⁰ C, preferably 65 ⁰ C, at which point the maleic anhydride melts. Stirring can be carried out, preferably when the melting point (60 G) is reached.

909837/1 5

After the dicarboxylic acid, for example maleic anhydride, has essentially completely melted, this can Dioctyltin oxide in amounts of 1OÖ-1O5 parts, for example 100 parts to be added to the reaction vessel

You preferably let amount of Dioctylssixmoxyds to be used essentially stoichlometrically equivalent to the carbonic acid or the anhydride. If maleic anhydride is used, the reaction proceeds according to the following equation:

CH

η (C ₈ H _{| 7} ) ₂ Sn0 + η

CH - C

Oh yes

- CH

where η is 2-4.

In the case of maleic acid, the reaction proceeds as follows

(C _Q H ₁₇ ) ₂ Sn0 + η ι!

CH -

CH -

C-OH

C OH

^x o

, OCO - CH, Sn- (I. 000 - CH

- 7 - n equals 2-4 let.

Preferably the Dioctylz-Innoxytt. given to the reaction vessel in portions τοβ 5-1OJi, for example 5Jt, the theoretically "usueetMnd amount"! Whenever the severity is carried out, we *, because I & re Qesmtaeage is suggested beforehand as well as the beginning of the reaction. During the reaction, the temperature of the reaction mixture is kept at about the melting point of the anhydride. For maleic temperatures of 7O-75 ° C, 75 ⁰ C ₁ Torcugeweise are. typical. The addition of the dioctyl chloride can be carried out during 2 (MO ain _t preferably 30 bin) Bach termination of the addition of the dioctyl lnojcyde sumV reaction mixture can ia case of a maleic anhydride y 'and di-n-octylcirmoyl containing ReektiojQSgejBilec.be under Rtiokf luB · 30-90 min, typically> 60 ain, to about 130 ° above sea level and preferably to 7O-T3O ° C _f for example 85 ⁰ C,

will hold. During the implementation, the resultant Solution will be very cloudy and amber in color. If maleic anhydride is used then the byproduct can be water separated by azeotropic distillation during this period will. ·

At the end of this reaction, preference is given to the reaction mixture a filtering agent such as diatomaceous earth is added. This equipment can be stirred for 5-15 min, preferably 5 ain.

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frequency of the solvent) to a temperature of 45-11O ⁰ O, preferably about 20-25 ⁰ C above the crystallization point, are cooled. The mixture cooled in this way can

• r

at this temperature through a filter ", for example, a pressure filter, to be filtered" wherein the temperature in the same, preferably during filtration at about 20-25 ⁰ C above the crystallization point - is -contents typically 60-100 ⁰ C ·

The piltrate can then be cooled to room temperature for 1 "nf" i "during 30-120 hours, before 90 minutes, while stirring. At the end of this period, the temperature for 4 ·· Reaktionsge20-30 ⁰ C, for example, be 25 ⁰ C. ₉ If the temperature of this reaction mixture passes through the range of 35-65 ° Q, then crystallization can occur and a thick slurry can be obtained, which is optionally diluted with a solvent. The slurry can then be further heated to 15-25 ° C, preferably 20 ^° C. and kept at this temperature for 50-90 min, for example 60 min. After crystallization, 20-60 parts of the solvent can be added to the pulp in order to obtain a more liquid consistency. The cooling of the reaction mixture results in an unexpected crystallization of the dioctyltin carboxylate product in pure form as a slurry of finely divided,

909837/1518

dust-shaped (separating seen under the microscope) claws, which can be obtained by filtration or decanting. During the recovery of the product, the inert aliphatic Hydrocarbon solvents kept in liquid form, and the crystals are not subject to the destructive and dissolving forces that would undesirably be present at higher temperatures, for example at a destination The formation of discrete individual crystals is desirable and important for efficient and rapid filtration.

The crystalline product can then be separated from the solvent, for example by decantation or, preferably, centrifugation to produce a substantially pure crystal filter cake which can be washed with fresh, inert aliphatic hydrocarbon flux and then dried. The cake is then preferably broken up and at 50-6O ⁰ C, preferably from 6O ⁰ C, dried.

The product dioctyltin dicarboylate appears as an almost white to orea colored crystalline powder obtained in a yield which is usually more than 95% and is more typical Way of approaching the stoichiometric yield. Are habitually the yields 90-98%. An analysis of a typical product shows that it contains essentially the calculated amount of tin

909837/1518

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and that it has essentially the calculated acid number These products also have Schaelapuiürte that fall into sharply defined areas.

The preferred product, dioctyl.KiTinaaleate, can be obtained as a near-white or creme-colored crystalline powder in yields which are usually more than 855 and typically approach the etochioic yield. Usually the yields are 90-98 *. Analysis «Ines typical JPro & ukts produced in this way» that it contains 24.95 * to 26.4 *, for example 25.9 * »tin (calculated 25.86 *) _o The saponification *» **! (i.e. SJtureahl) came out 254-250, for example 245 (calculates 244). In the case of di-n-octylamine maleate, the product has a carbon point of 93-96 ° E.

The new dioctyltin gea & S of the invention are obtained as in essentially pure _9-free llieflende materials with a nearly white to creaigen color. On the surface, the product looks like a powder. However, observation under a microscope shows the presence of 7on crystals, which are typically orthorhombic trianes. In the case of the new di-n-octylsinnoaleate, the product can be obtained in the form of hexagonal prisms, depending on the solvent. The prisms are represented by an X-ray diffraction diagram

909837/1511 '

which has characteristic peaksIn the case of the preferred di-n-octylzinnaaleate, the SpltBen are at 13.6 Ϊ, 6.86 A and 4.6 A in a wide range of τοη solvents, including cyelohexane, isopsr £ or solvent 210, find su. Ib lall «τοη Di-n-öctjleinnadipat the X-ray spectrum has peaks at 12.4» 4.12, 6.31 * 3 »51, 8.05 and 4.56 A (in the order of decreasing intensity). In the case of dioctyltin succinate, the X-ray spots are 13.7, 6.69, 4.48, 4.74, 4.27, 8.3, 7.98 and 3.37% in the order of decreasing intensity.

These products typically have snfcnrf "ftpsswl" points within a narrow range ·· I · lall * τοη di ^ n-ootyltin maleate, the melting point is 93.5-95.5 ° C.

The solubility of these raw materials can be different. Typical is Dl-n-kKJtylminnsaleat, «« loh ·· in warm aromatic Hydrocarbons, called aliphatic solvents, «1 · s.B. Heptane, and cold zetones, such as s.B. Methyl ethyl ketoa, is soluble. i

[ Determination of the molecular weight of these new compositions! can be carried out by osmometric technology, whereby the compositions can be dissolved in benzene.

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waits for these materials to have molecular weights that two to four times the formula weight. Usually, they have molecular weights which change with recrystallization. In one case, for example, I changed the Molecular weight from 3.65 to 2.67 after recrystallization made of heptane »

The invention is further illustrated by the following examples in which all parts are expressed by weight, provided. nothing else is stated.

example 1

According to this example, which reproduces a preferred implementation of the process according to the invention, 2200 parts by weight of commercially available heptane with a low aromatic hydrocarbon content are introduced into a reaction vessel together with 610 parts (8.25 hol) of maleic anhydride. The reaction mixture is heated to 60-65 ⁰ C and stirring is begun BObald as maleic anhydride, melted sufficiently 1st. After the maleic anhydride has melted almost completely, 2980 parts (8.25 mol) of di-n-octyltin oxide are added to the reaction vessel. The di-n-ootyltin oxide is preferably added in amounts of 51 %, that is to say that the individual amounts are 180-200 parts by weight. The addition of this material is controlled so that the temperature is maintained at 70-75 ° C. Preferably the addition

'"copy

performed during 20 * 40 τη-tn . The addition of di-n-octyl tin oxide at this rate during this period is sufficient to keep the reaction mixture in the liquid state. Hachdeo the oxide has been completely sugegeben the Reaktionsgwaisoh is a further hour · the reaction mixture stirred at 80-85 ⁰ C. During this time the reaction mixture is colored amber and very cloudy.

After 60 min, are added 2 parts by weight 0 _r Diatoaeenerde-Fil trier Helpful Emean the reaction mixture, which is then stirred for a further 5 minutes while ee is allowed to cool to 65 ^0C. The reaction mixture is then filtered through a heated before pressure filter, which is maintained at a temperature of 60-70 ⁰ C.

The filtered solution is slowly cooled to room temperature over 90 minutes with stirring. When the pil is ^{cooled to 35-4O 0} C, crystallization occurs (with a mild exothermic tint). The reaction mixture becomes thick at 3O ⁰ C. Another 600-800 parts of solvent are added at this point to dilute the pulp to a more fluid consistency. A further cooling is then carried out to 15 ° C., and the Qealech is kept at this temperature for 1 hour. The mixture cooled down on this catfish is filtered off and the filter cake is washed with 300 parts by weight of solvent and dried. The filter cake is broken, is then dried at 50-6O ⁰ C. In this way, 3411 parts by weight (90.6 # yield) of the product

9098 3 7 / 1-5 ^ W _C0PY

Dukts di-n-octyltin maleate with a melting point clay. 95-96 C and a tin content of # 26.15 (theory £ 25.86). The acid number is 245 (theory 244). * ^; _y

Example 2

According to this example, which represents another preferred embodiment of the process according to the invention, 2930 Qmr, - parts of Isopar E solvent (commercial mixture of Cg isoparaffins) together with 817 parts (8.33 mol) of maleic anhydride are introduced into a reaction vessel ^c Reaktionäre- mixture is heated to 60-65 ⁰ C, and stirring is started as soon as the maleic anhydride is sufficient geschmolsen. After the maleic anhydride has almost completely melted, 2980 parts (8.25 mol) of di-n-octylzian oxide are added to the reaction vessel. The di-n-cotylin oxide is preferably added in 5% of the total amount, ie d * 8 typical 180-200 parts by weight. The addition of d * e material 'o is controlled so that the temperature is kept at 70-75 ⁰ C. The addition is preferably carried out over a period of 20-40 minutes. The addition of di-n-octyltin oxide at this rate and during this period is sufficient to keep the reaction mixture in a liquid state. Once the oxide has been completely added the Seaktionageniseh is the fieaktlonegenlsch stirred an additional hour at 85-95 ⁰ C. During this time the reaction mixture turns amber and very cloudy.

909837/151 8 ORIGINAL INSPECTED

At the end τοη diatomaceous earth filter aid is 60 nin added in an amount of 0.2 parts by weight of the reaction mixture 'was stirred for 5 min and then · which is then allowed to cool down to 65 ⁰ C. The reaction mixture is then filtered through a Torerheated pressure filter which is kept at a temperature of 60-7O ⁰ C.

The filtered solution is then cooled slowly during 90 min under Rübren to room temperature _o When the filtrate cooled to 35-4O ⁰ C, crystallization takes place and the Reaktionsgemisoh becomes thick at 30 ° 0th Another 200-400 parts of solvent are added to the thin paste to make the consistency more fluid. Bs is then further cooled to 15 ⁰ O, and the mixture is kept at this temperature for 1 hour. The mixture cooled in this way is filtered and the filter cake is washed with 30 parts by weight of solvent and then dried.

The filter cake is broken up and then at 50-6O ⁰ C dried. In this way, 3690 parts by weight (98.5 * yield) of the product di-n-octyltin maleate with a Sohmelsponkt τοη 93-95 ⁰ C wad a tin content τοη 25.8 * (theory 25.86Jt) are obtained. The star number is 249 (theory 244).

Example 3 * '

According to this example, which is a further embodiment of the

represents inventive method, 2200 parts by weight of cyclo-

109837/151 «

hexane was introduced into a reaction vessel along with 817 parts (833 moles) of maleic anhydride. The reaction mixture is heated to 6C-65 ° C and stirring is started as soon as the maleic anhydride has sufficiently melted. After the maleic anhydride has almost completely melted, 2980 parts (8.25 mol) of dioctyltin oxide are added to the reaction vessel. Preferably, the Dioctylzinnoxyd in Kiengen of 5% is added to the total amount ·, d _o h., That a typical amount of addition is 180-200 parts by weight. The addition of this material is controlled in such a manner that the temperature is kept at 70-75 ⁰ C. The addition is preferably carried out over a period of 20-40 minutes. The addition of the oxide at this rate and during this period is sufficient to keep the reaction mixture in a liquid state. After all of the oxide has been added to the reaction mixture, the reaction mixture is ^{stirred at 80 °} C. for a further hour. During this time the reaction mixture turns amber and very cloudy.

After 60 min 0.2 wt "are - Dlatomeenerde parts filter aid are added to the reaction mixture which is then stirred for 5 min, during which it at 65 ⁰ C is allowed to cool. The reaction mixture is then filtered through a preheated pressure filter kept at a temperature of 60-70 ° C.

The filtered solution is slowly stirred over 90 minutes

809837/1518 _copY

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cooled to room temperature. When the filtrate ^{cools to 35-4O 0} C, crystallization occurs and the reaction mixture becomes ^{thick at 50 0} C. A further 600-800 parts of solvent are added in order to dilute the slurry to a more fluid consistency. It is then further cooled to 15 ° C., at which temperature the mixture is filtered and the filter cake is washed with 300 parts by weight of solvent and then dried.

The filter cake is broken up and then dried "at 50-6O ⁰ C, In this way, 3560 parts by weight (90.6 ^ AuBbeute) dee dioctyl product with a melting point of 93-95 C and a tin content of 25.54 * (Theory 25 _r 86 #) The acid number is 246.7 (theory 244).

From the above examples it is evident that it is possible to use the new process to obtain pure dioctyltin maleates directly from one Obtain reaction mixture by crystallization. It is not necessary to distill off the solvent, nor the product during to age for a longer period of time or to redistill the product, in order to obtain the desired purity, as is customary with those previously known / experienced for the production of materials of this type was.

Example 4

According to this example, which is a preferred implementation f (■■■.

COPY 909837 / 15ΐβ

of the process according to the invention, while 150 parts by weight of a commercially available heptane together with 40 * 4 parts (0.277 mol) of adipic acid are introduced into a reaction vessel. 100 parts of di-n-octyltin oxide are added. The Ileaktlonsgeaieeh is heated to reflux (85 ⁰ C). The reaction water is removed for 200 s by condensation in a Dean-Stark palle. The Tenperatur the reaction then rises after 5 parts of water are collected at 97 ⁰ C. This gives a clear yellow solution. The solution is cooled to 75 ⁰ C, and 0.2 parts of diatomaceous earth are eye type, the solution is filtered and slowly cooled. Crystallization occurs at 43 ° C. ~

Here an exothenae ifärE ^ t ^ uisg jaaf occurs , which increases the temperature to 52 ⁰ C. 50 parts of heptane are then added and the mixture is cooled to room temperature for 1 hour. The mixture thus cooled is filtered and the filter cake is washed with a small amount of solvent and then dried.

The filter cake is broken up and dried at 50-60 ° C this becomes 129.4 parts by weight (95.6% yield) of a product with a melting point of 75 ° C and a tin content τοη 24.262 * (Theory 24.2696). The acid number is 240 (theory 229).

The molecular weight (osmomitriseh in chloroform) is 692.

90 * 837/15 TS bathroom original

Example 5

According to this example, which represents a preferred embodiment of the process according to the invention, 75 parts by weight of Ieopar S (a commercially available mixture of iso-ethanes) are mixed with 28.2 parts (0.28 parts) of succinic anhydride in introduced a reaction vessel. The Reaktionegeaiseh is heated to 12O ⁰ C, and the agitation is started as soon as the anhydride sufficiently melted 1st. When the anhydride has almost completely melted, 100 parts (0.28 mol) of di-n-octyltin oxide are added to the reaction vessel. The di-n-octyltin oxide is preferably added in amounts of 1% t of the total amount over the course of 0 min. The addition of τοη dloctyltinozide at this rate during these periods is sufficient to keep the reaction chemical in a liquid state. Hachdea the oxide completely the Reaktionflgeelech did added, the Reektionegealsch · tin · hour · is further stirred at the Rückflufiteaperatur of 135 ⁰ C, which temperature is reached · min after 90th At the ·· «point in time, the mixture of reactions became clear.

The mixture is ^{cooled to 120-125 0} O, and Dioalit mtrierhilfsmittel in an amount of 0.2 parts by weight is the. Reaktionsgemlech added which is then filtered through a preheated pressure filter, which is maintained at a temperature of 125 ⁰ G.

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The filtered solution is slowly cooled with stirring over a period of 30 minutes. When the filtrate has ^{cooled to 106 0} , crystallization occurs. 100 parts by weight of etching solvent are added. It is then ^{cooled further to 15 0} O, at which temperature the mixture is filtered. The filter cake is washed with a small amount of the solvent Isopar £ and then dried.

The filter cake is broken up and bsi 5O ⁰ C dried · Bs are in this catfish 123.6 parts by Gw. (97 * yield) · a "products with a quick point τοη 140 ⁰ C and Onea tin content tob 25.71 * (theory 25 , 74 *) received. The acid number is 240 (theory 243).

The molecular weight (osmometrisoh in chlorof ons) is 954 *

909837/1515

Claims (1)

Claims ο Process for the production τοη Dloctylsindioarboxylaten, characterized in that nan la substantial atochiometric amounts of dioetyltin oxide and Dlcarboxylic acid or dioarboxylic anhydride in the presence of a Inert aliphatic carbon dioxide solvent is used as a reaction medium, with diootyltinndloarboxylate being formed will; that the named reactions & edium after completion the reaction cools down, whereby the said dioctyl dicarboxylate precipitates; that said crystallized dioctylsine dicarboxylate is obtained as a product; and that nan while this extraction keeps the inert aliphatic © hydrocarbon solvent in the liquid phase 2. The method according to claim 1, characterized in "that the inert aliphatic Kohlenwaeeerstoffiesmittel 5-16 carbon atoms" contains. Process according to claim 1, characterized in that the inert aliphatic hydrocarbon fluid contains 6-8 carbon atoms. 901837/1518 4. The method according to claim 1, characterized in that the inert aliphatic sole watering agent is a straight-chain aliphatic · Kbhleniras * serstoffl6ungsaittcl is · 5. The method according to spoke 1, characterized in that the inert aliphatic lohltnwmeeerstofflusungenlttel is heptane. 6. The method according to claim 1, characterized in that the inert · aliphatieche Kohlcnva ··· - atofflöaunganittel a boiling point of iraniger al · beaitst 15O ⁰ C. 7 * The method according to claim 1, characterized in that the inert · aliphatic · IohlonimaserflOeungsBittti. a leoparaffean hydrocarbon is. 8. The method according to claim 1, characterized in that the tea temperature dee Aealctionsgemis ^ s is held at about 6O ⁰ C. 9. The method according to claim 1, characterized in that the temperature of the reaction level is kept below 130 ° C. 909837/1518 10. The method according to claim 1, characterized in that the dl · temperature of the reaction mixture is kept at 60-10O ⁰ C. 11. The method according spoke 1, characterized in that, after the end of the reaction, the reaction mixture is cooled to 15-4O ⁰ O, at which temperature the dioctylsine diearboxylate is obtained in crystalline form. 12 · Method according to claim 1, characterized in that · the ratio τοη solvent see below Product which is 0.55 t and 2 t 1 cold 13. Process according to one of the preceding claims, characterized in that malelic acid anhydride is used as the dioarboxylic acid anhydride. 14. Free-flowing diootylsinndloarboxylate, thereby known that there was a near-by to creamy color, on the surface a crystalline structure and also orthorhombisohe, prissdsohe or Has hexagonal prismatic crystals. 15. Free-flowing di-n-octyltin oil, characterized in that it orthorhOBishe crystals when it is crystallized from heptane. 909837/1513 16. Free-flowing di-n-octyltin maleate, characterized by £. «- indicates that it bit almost white creamy color, a molecular weight equal to 2-4 foraelgewiehten and X-ray diffraction peaks in the series of decreasing intensity at 13.6X, 6.86X and 4.6X. 17. Free flowing di-n-octyleinnadipat, characterized in that it is an almost white to eremige color, a molecular weight equal to 2-4 Foroelgewiohten and Euntgenetrahlenbeiffiffungspitzen in that order decreasing intensity at 12.4X 4 »12 S, 6.51 S, 3.51?, 8.05 l and 4.5 l. 18. Free flow © nde β Di-G-octylJsinneucoinÄt, characterized in that it has a near w # ifie to orange color, a molecular weight equal to 2-4 Forael weighed and X-ray diffraction apex in the order .. of decreasing intensity at 13.7A, 6.69A, 4.46A, 4.74X, 4.27X, 7.89X and 3.57X. UHMMUtNCKE, WL-Me. MOM MTL-ΙΝβ. VSTACKMi 309837/1518