JPS60184089A - Hydrocarbon-soluble dialkyl magnesium compound - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION Diorganomagnesium compounds are well known as useful in a variety of chemical reactions.

As reaction reagents, these compounds can be used for the reduction of ketones, the methylation of aromatic compounds, the alkylation of metal oxides and metal oxides to the corresponding alkyl metals, and the like. As catalysts, diorganomagnesium compounds are useful in the diminution and polymerization of olefins (UK Patent No. 1.251.177);
Polymerization of synthetic boxy compounds (U.S. Pat. No. 3.444.102)
); and the production of telomers (U.S. Pat. No. 3,742.);
No. 077). These compounds have the same type of function as Grignard reagents, but due to electronic and steric factors, Grignard reagents are more active against certain compounds. See generally U.S. Pat. Nos. 3.646.231 and 3.822.219.

Many diorganomagnesium compounds are tetramorphic or viscous liquids, and all are unstable when exposed to moisture or air, reducing their usefulness. This problem is generally solved by dissolving the compound in an inert hydrocarbon solvent or removing the solvent and handling it in an inert atmosphere. Many diorganomagnesium compounds, (K, those with lower linear argyl up to 4 carbon atoms) are insoluble by themselves in hydrocarbons;
Requires a solubilizer to form a soluble complex. Examples of such solubilizers include alkyl lithium compounds (U.S. Pat. No. 3,742,077); dialkylzinc compounds (U.S. Pat. No. 3,444,102); alkali metal halides (U.S. Pat. .655.790): and organoaluminum compounds (U.S. Pat. No. 3,737.3)
No. 93). Solvation involves directly involving the magnesium atom to form a liquid phase complex, and uses ether or organic base molecules. However, solvated compounds are not preferred because they inhibit the effects of this compound, especially when used as a Ziegler type catalyst.The use of ethers is particularly undesirable from the standpoint of flammability and explosiveness. According to Schlenk's equation, soluble RMgX is produced, which is undesirable.

R, Mg + MgX, ::2RMgX, where R is alkyl and X is halogen, can lower the viscosity of the reaction mixture by solubilizing it, otherwise the reaction will not proceed due to the high viscosity. solubilization solves this problem. This problem can be solved to some extent, although incompletely, by suspending the insoluble compounds into low viscosity suspensions using allyl chloride solvents (U.S. Pat. No. 3,264,366).
No. 0).

Furthermore, the insolubility of lower alkylmagnesium compounds
This makes it difficult to avoid unnecessary halides in the manufacturing process. The direct reaction between magnesium metal and organic halides was published in the Journal of Organometallic 1 Chemistry.
rgano metal-1i c Cltemis
try cl;+ze and 3e1man,)yo
l, 5, p, 477 (1966) and the same, VOl,
64, p, 25 (1974) (W, N, Sm1th
). The Kore et al. paper describes the preparation of diorganomagnesium compounds having linear alkyl groups of 5 or more carbon atoms. These compounds are soluble in hydrocarbon solvents and can be separated from co-produced magnesium halide and unreacted magnesium.

When used in the lower linear alkali Kaneki process, the desired diorganomagnesium compound is produced, but it is insoluble and therefore exists as a slurry in the solvent together with the magnesium halide and unreacted magnesium metal. Therefore, when producing a lower alkyl diorganomagnesium compound using this process, a solubilizer is required. The latter are useful as reactants or catalysts because they have a relatively high magnesium content on a gravimetric basis.

V of the song! Mercury-magnesium exchangeability (Journal of Organic Chemistry) (('
owan and Mo5her) vol, 27, p.
, 1 (1962), and the Diogisanate Precipitation Method (Berichte der Deutschen Hemidien Gesellschaft) (Berichte der [)eutsch
enChetnischen Ge5eJIschaf
tXschJeuk) Vol, 64, p, 734 (1
931).

Mercury method R2Hg 10Mg-+R2Mg + Hg (where, R
1 is an alkyl, and there are restrictions due to the high price of dialkyl mercury and the health hazards when using it. The reaction itself is dangerous because, after a period of inhibition, it proceeds rapidly and exothermically.

In the following dioxanate precipitation method, where R is alkyl and X is halogen, magnesium halide is removed from the Grignard reagent by complexing and precipitating dioxane with the halide. Since this process produces etherified dialkylmagnesium complexes, the ether must be removed before use as a catalyst.

Dialkylmagnesium Vi-t can also be obtained by precipitating lithium halide from alkyllithium (US 1±1 Patent No. 3.646.231) MgX2 + 2t, i R-1 →, R, Mg +
2LiX (where R is alkyl and X is halogen), which is a linear lower dialkylmagnesium. This document also describes the use of hydrocarbon-soluble diorganomagnesiums to solubilize hydrocarbon-insoluble dialkylmagnesiums. The solubilizing agents shown here always contain nucleated alkyl groups. Such branched diorganomagnesium compounds include the above-mentioned glaze (Qlaze) and se/l/? 7 (sel
It cannot be prepared using the man method. This has been demonstrated by Kamienski and Eastham (B.
(asthatn) version of the report (Journal of □rga
nicCheJnjStr,y) VOl, 34, p
, 1116 (1968). Therefore, it is necessary to rely on the lithium halide precipitation method.

A similar method is described in US Pat. No. 3,742,077. The solubilizing agent must also be a branched dialkylmagnesium which is soluble in hydrocarbons, such as di-tertiary butylmagnene, di-secantylbutyl-7, and di-butyl-7.

The reason that linear lower alkyl magnesium compounds are generally highly soluble is said to be due to the fact that the magnesium atom is surrounded by four argyl groups, forming a polymer-like macrostructure. The first known method to solubilize these compounds is probably because they break these intermolecular bonds and make the macrostructures smaller. The solvation and complexation described above are thought to bring about this effect.

Alkylmagnesium compounds having a branched argyl group or a straight-chain alkyl group having 5 or more carbon atoms are effective as solubilizers, but they are also thought to have the effect of breaking the parent intermolecular bond. ing. However, in the case of the compound argylmagnene, this effect &:t, due to alkylation and recombination, in this case the i, r-solubilized alkyl group is said to exchange positions with the linear lower alkyl group. ing. The substituted groups are too bulky to fit around the magnesium atom, or the groups have their own solubility, sterically preventing conjugation.

U.S. Pat. No. 4,069,267 discloses for stabilizing (precipitation prevention) di-n-butylmagnesium/di-secondary-butylmagnesium and di-n-butylmagnesium/di-tertiary-glutylmagnesium compositions. ,
The use of longer chain dialkylmagnesium compounds is disclosed. Long chain dialkylmagnesium compounds with 6 or more carbon atoms in the alkyl group, preferably
It has 8 or 10 machetes.

This process uses relatively expensive branched alkyllithium compounds, such as 2-butyllithium and 3-butyllithium (1), which contain the presence of higher alkyl chlorides. is added to the reaction product of magnesium metal with branched sialyl magnesium compounds (e.g. di-tert-butyl and di-tert-butyl).
Although these branched alkylmagnesium
It cannot be obtained by direct reaction of magnesium with the corresponding secondary or tertiary alkylnolide in a hydrocarbon solvent. The three-component magnesium alkyl composition described in U.S. Pat. No. 4,069,269 also includes two dialkylmagnesium compounds that are individually soluble in hydrocarbons. It is therefore not surprising that three-component compositions dissolve very well in such solvents.

Several other U.S. patents disclose hydrocarbon-soluble sialylmagnesium systems containing two or three components -C, where the alkyl group is a C1-4 straight chain alkyl and another dialkylmagnesium The alkyl groups of the compounds differ by one or more carbon atoms.

No. 4,127,507 discloses a composition containing di-11-butylmagnesium and diethylmagnesium. U.S. Patent No. 4,207.20
No. 7 describes a composition containing di-n-propylmagnesium and dimethylmagnesium. U.S. Pat. No. 4,222,969 discloses compositions containing di-n-butylmagnesium and dimethylmagnesium. Also, U.S. Patent No. 4.207.207
A ternary hydrocarbon soluble magnesium alkyl system containing di-n-propyl-, diethyl-1 and dimethylmagnesium is disclosed. However, the yield of soluble dialkylmagnesium in this three-component system is relatively low, at most about 25%.

Furthermore, when dealing with the two-component lower alkylmagnesium compositions described in these three patents, the yield of hydrocarbon-soluble dialkylmagnesium compositions is limited to a relatively narrow molar range of the two starting alkyl halides. It has been found that the best results are obtained within a range of ratios. In U.S. Pat. No. 4,127,507, the maximum yield of soluble dialkylmagnesium compositions is approximately 0 for n-butyl:ethyl molar ratios, especially from Examples 2-8.
．． It can be seen that a range of about 8:1 to about 1.25:1 can be obtained, particularly about equimolar ratios.

On the other hand, if the molar ratio is about 3:1 and either n-butyl or ethyl chloride is increased, the yield of soluble dialkylmagnesium is about half that of the optimum ratio. Also, at a molar ratio of about 10:1, the yield is only a few percent.
It only becomes. The same thing happens with di-n-propyl/dimethyl and di-n-butyl/dimethylmagnesium.

Furthermore, in Examples 3 to 5 of U.S. Patent No. 4,222,969, when the two dialkylmagnesium compounds differ by only one carbon number in the alkyl group,
It has been shown that hydrocarbon soluble compositions are not obtained.

In some cases, depending on the process in which the hydrocarbon-soluble dialkylmagnesium composition is used, it is advantageous to prepare a composition in which -C is dominated by one of the two alkyl groups. For example, if a dialkylmagnesium compound is used as an alkylating agent in a hydrocarbon solution, it is advantageous to obtain a hydrocarbon-soluble composition rich in the desired alkylmagnesium. When producing certain types of polymerization catalysts, it is preferable to use a composition in which one or the other of the two-component compositions contains more dialkylmagnesium. If the goal is to obtain a hydrocarbon-soluble dialkylmagnesium composition with a high magnesium content, a dialkylmagnesium gold-rich composition with smaller alkyl groups is preferred.

According to the present invention, it contains three or more sialgyl magnesium compounds, where about 75 to 95 mole %
the composition of which contains two or more dialkylmagnesium compounds;

Each of the argyl groups is a C7-4 straight chain alkyl (hereinafter referred to as "lower dialkylmagnesium compound"), and about 5 to 25 mole percent is at least one dialkylmagnesium compound, which has 5 carbon atoms. Alternatively, dialkylmagnesium compounds having more than one straight chain alkyl group (hereinafter referred to as "higher dialkylmagnesium compounds").

In a preferred embodiment, the composition comprises about two different lower dialkylmagnesium compounds, such that the number of carbon atoms in the argyl group of one compound differs by at least one from that of the other compound. and a higher dialkylmagnesium compound whose alkyl group is an ih chain alkyl having 5 or more carbon atoms.

In a more preferred composition, one of the lower dialkylmagnesium compounds of 24t4 is about 70-93 mole percent;
Other lower dialkyl magnesium is about 2 to 20 mol%
The high dialkyl magnesium component is approximately 5 to 2
It is 5 mol%. In the most preferred composition, one of the two lower dialkylmagnesium compounds has a molecular weight of about 70 to 90
The mole percent ranges from about 5 to about 20 mole percent.

This invention relates to dialkylmagnesium compositions that are soluble in hydrocarbon solvents and contain three or more dialkylmagnesium compounds. Preferably, these compositions include three dialkylmagnesiums,
Contains two lower dialkyl compounds and one higher dialkyl compound.

The term "hydrocarbon solvent" means aliphatic, cycloaliphatic, and aromatic hydrocarbons. As an aliphatic solvent, n-
Examples include pentane, impentane, n-hexane, n-hebutane, low octane, isooctane, pentamethylhebutane, gasoline and other petroleum fractions. Alicyclic solvents include cyclohexane, methylcyclohexane, methylcyclopentane, cycloheptane, and cyclooctane; aromatic solvents include benzene, toluene,
These include xylene, ethylbenzene, tetralin, methylnaphthalene, etc.

Preferably, it has 5 to 20 carbon atoms, and preferably C8 to 1. A particularly preferred solvent is one having a boiling point of 69°C to 110°C.

The concentration of dialkylmagnesium in the solvent is not critical and is generally soluble within a wide range.

However, as the concentration increases, so does the viscosity.

Therefore, from the viewpoint of ease of operation, the concentration of dialkylmagnesium is usually about 0.2 to 15
．． 0% by weight, preferably about 1.0-5.0% by weight
It is. However, if the solution has a higher dialkylmagnesium concentration, its viscosity can be reduced as follows.

Various methods are utilized to prepare solutions of multicomponent dialkylmagnesium compounds in the desired hydrocarbon solvent.

In one method, a solution is prepared by physically combining a dialkylmagnesium compound and a hydrocarbon solvent. Dialkylmagnesium compounds can be used in relatively pure form, or in solid or slurry form, depending on the method of production.

Whatever form the dialkylmagnesium compound takes, it can also be used in its individual state, for example in the insoluble form of di-n-butenemagnesium or diethylmagnesium;
Di-n-hexylmagnesium solid) or two or more dialkylmagnesiums prepared in combined form by mixing with higher dialkylmagnesiums such as di-n-hexylmagnesium in a hydrocarbon solvent. Insoluble components present in the compound are separated and a clear solution is obtained. For example, a solid or slurry of di-11-butylgnesium mixed with magnesium/.ride, other insoluble by-products, or unreacted starting materials, such as diethylmagnesium, di-11-butylgnesium, By contacting with a hydrocarbon solvent in the presence of magnesium, a product containing dialkylmagnesium as a solute and substantially free of other components can be obtained. Heating the solution to about 50°C or above 4F will speed up the dissolution. Once a compound dissolves, it remains in solution even if the temperature is lowered.

If desired, separation of insoluble material and solution can be accelerated by the use of viscosity reducing agents known in the art. Examples of viscosity reducing agents include trialkylaluminum nicums, sialylthylaluminum halides, alkylaluminum cybarides, and the like.

Further, the dialkylmagnesium compound can be prepared directly in a solvent in a conventional container by simultaneous or sequential reactions. Reactions such that no by-products or unreacted starting materials are dissolved in the final mixture are suitable. In this way, insoluble matter can be easily separated by Kp. One such technique is
It is a reaction between magnesium metal and a suitable alkyl halide. The simultaneously produced magnesium chloride precipitates and can be easily removed from the solution together with unreacted magnesium. Another method is to use a Grignard reagent to introduce the alkyl group of l). Grignard reagent FA
The ether used in the preparation needs to be removed before carrying out the main reaction. The reaction product of the alkyl halide and magnesium metal is reacted with a Grignard reagent to obtain the desired solution of the dialkylmagnesium compound. Commercially available magnesium cuttings may be used to directly react magnesium with the alkyl halide. However, it is preferable to use a material with a larger surface area than these. This can be achieved by grinding. However, most preferably
It is best to use a fine powder of 150 microns or more.

If magnesium is to be reacted continuously, the alkyl halide with the largest number of carbon atoms, i.e., CS
It is reacted with an alkyl halide having the above-mentioned straight-chain alkyl group, then with an alkyl halide having the next highest number of carbon atoms, and sequentially down to the alkyl halide having the smallest number of carbon atoms. A magnesium activator is used to initiate the reaction. Higher alkyl halides react more easily with magnesium than lower alkyl halides, so care must be taken to prevent runaway reactions. This can be achieved, for example, by using a large amount of solvent, by extra stirring, by slow addition of the alkyl halide, or by adding excess magnesium.

A "magnesium activator" is a substance that causes the alkylnoride to react at a faster rate when heated or in contact with the magnesium.

Many activators are known. A typical example is AAα3
, Atα, -ether complex, N,N-dimethylaniline, molecular iodine, an alkyl halide of at least Cs and a Grignard reagent. Higher dialkylmagnesiums such as di-n-hexylmagnesium itself act as activators, as described in Example 2 of US Pat. No. 4,207,207.

Activation by heating is also used. Generally about 125°
The temperature is between 350°C and 350°C. Preferably about 150°
~250°C, the most feminine temperature is 150°~200°C. Once magnesium is activated, the magnesium/alkylnolide reaction proceeds at lower temperatures.
Most preferably it is about 80° to 130°C. At least 10% by weight of alkyl-ride based on the weight of magnesium should be present during heat activation.

The temperature ranges mentioned above are not essential.

The lowest temperature should be considered from the economical point of view of the process, and the highest temperature should be considered from the viewpoint of the possibility of decomposition of the alkyl/ride and from the point of view of energy saving.

Preferably, the alkyl halide is reacted simultaneously with magnesium in the desired ratio to form the composition. Alternatively, the higher alkyl halide is first contacted with the magnesium, from which the remaining alkyl halide is added as a mixture. Remove minutes. The resulting dialkyl-magnesium compound is then diluted or concentrated to the desired concentration, taking into account reactivity, viscosity, or economic considerations.

The word ``halide'' refers to chloride, promide, iodide, or any combination thereof. Fluoride is usually preferred for economic reasons.

The molar ratio of magnesium to alkyl halide can vary over a wide range. No matter which reaction is performed, there is no particular strict range. However, usually the molar ratio of magnesium to total halides, t, is about 1.0-2.
(), preferably about 1.1 to 1.3. A molar excess of magnesium greater than 1.0 has the effect of minimizing Wurtz coupling reactions.

The hydrocarbon solvent may be added before, during or after the reaction. M is also preferable, since if a solvent is added before or during the reaction of the initially added alkyl halide with magnesium, the subsequent reaction may be slightly inhibited due to viscosity.

Magnesium is a substance that can instantly combust on contact with air traps. To prevent such combustion and oxidation of the dialkylmagnesium, the reaction must be conducted in the absence of traces of oxygen. The reaction is therefore usually carried out in an inert atmosphere such as nitrogen, argon, or argyl halide gas. The reaction must also be carried out in substantially anhydrous conditions since the dialkylmagnesium reacts with water. The pressure at which the reaction is carried out is not critical and ranges from normal pressure to high pressure of several atmospheres. Most preferably, the pressure is slightly higher than atmospheric pressure to keep the argyl halide in solution. Preferred pressure range is about 8 psi
*g (1,6X 105 Pascal) to about 1100p
It is in the range of si9 (8, OX 1.05 Pascal).

The lower sialgyl magnesium compound in the composition of the present invention contains a C1-4 straight chain alkyl group. For example, combination alkylmagnesiums such as dimethylmagnesium, diethylmagnesium, di-n-propylmagnesium, di-n-butylmagnesium and n-butylethylmagnesium, n-propylmethylmagnesium, methylethylmagnesium. The compositions of the invention contain at least two such dialkylmagnesiums.

The t\-grade dialkylmagnesium has a linear alkyl group of n, c or more, preferably C3 to 79, most preferably C6 to 1°. For example, di-n-amylmagnesium, di-n-hexylmagnesium, di-1-octylmagnesium, and the like. fd2 with these monsters
Preferably, the two alkyl groups are the same.

Hydrocarbon soluble compositions according to the invention generally have about 75%
~95 mol% lower dialkylmagnesium compound (2
or more compounds) and about 5 to 25 mole percent of at least one higher dialkylmagnesium compound.

This composition contains a large amount of any one selected lower sialgyl magnesium compound,
About 70-93%, the most suitable size is 70-9Qi = % is one lower dialkylmagnesylano compound, about 2%
~20, most preferably about 5 to 20 mole percent fd is also the other lower dialkylmagnesium fraction, and about 5 to 25 mole percent is higher dialkylmagnesium.

In the compositions of the present invention containing diethyl-, di-n-phthyl, and di-hexyl-magnesium, as low as 5 mol% di-n-bekfulmagnesium and as high as 93 mol% The composition may be di-n-butyl or diethylmagnesium, or the other may be as low as 2 mol % of lower dialkylmagnesium. Most preferably, for use as a polymerization catalyst, the composition contains a high content of dilobylmagnesium and a low content of diethylmagnesilano.

The compositions of the invention may contain lower dialkylmagnesiums in which the number of carbon atoms in the alkyl group differs by only one. Such combinations are, for example, dimethyl/diethylmagnesium, di-n-probyl/di-+1-butylmagnesium, sium or diethyl/di-n-probylmagnesium, and the like. As shown in Examples 3-5 of U.S. Pat. No. 4,222,969, two-component compositions containing only these forms of di-f-alkylmagnesium are insoluble in hydrocarbons. The present invention, however, provides hydrocarbon soluble compositions containing such combinations of dialkylmagnesiums.

Next, the present invention will be further explained by examples.

Example 1 (Comparative Example) This example shows the preparation of a mixture of dimethyl and diethylmagnesium according to the prior art and is described in US Pat. No. 4.222.
．． This corresponds to Example 5 of No. 969.

A pressure vessel equipped with a variable immersion tube, a thermometer, and a stirrer was placed in an oil bath, purged with four gases, and heated to 13.0? (0
, 53F-atoms) is added. A small amount (
0,24jj) di-n-hexylmagnesium i18
Add 4 f of hebutane to activate the metal and remove all moisture. The vessel is heated to 1 (+) 1-110° C. While maintaining this temperature, J 3.3 f (0.21 mol) of 1 thyl chloride is slowly added over a period of 2 hours.

Following the addition of ethyl chloride, the total
Heat to 0° C. and add 6.6 r (0.13 mol) of methyl chloride over 2 hours. The reaction mixture is then kept at 130°C for 6 hours.

Analysis of the solids in the reaction mixture and sampling of the clear hydrocarbon layer revealed only 0.03% by weight of magnesium, about 15% of the theoretical yield.

Solubilize by adding solid Kokin and tri-low octyl aluminum. When the obtained solution was analyzed, it was found that 0. ．． 83% by weight of magnesium (approximately 4% yield), methane:ethane moles 1-jO, 3:1 in the hydrolysis gas, indicating that dimethylmagnesium and diethylmagnesium were formed as an insoluble mixture.

Example 2 11m of a composition containing dimethyl-, diethyl-, C-Il-amylmagnesium Using an apparatus and method similar to Example 1, the following alkyl chlorides were prepared under pressure in the order and total of F. added to the container. = lower milk chloride (19%), ether chloride (19%), methyl chloride (62%).

Analysis of the viscous supernatant gold revealed that the magne/rum content was 1.1.
Analysis of the volatile hydrocarbons resulting from hydrolysis revealed 43% methane, 35% ethane, and 22% 11%, corresponding to a 4I% yield of soluble magne/lam alkyl at 8%.
- It was pentane. The magnesium (', nm-) in these +iJ-soluble dimethyl/diethyl/di-I+-amylmagnesium compositions was 27.4%.The lower dialkylmagnesium in this composition was 81 mol%,
and di-n-amylmagnesium was 19 mol%.

Example 3-7 The following experiment was carried out using the same method as described above, using a mixture of ethyl, ropetyl chloride, and rhohexyl chloride, and for comparison, using a mixture containing only ethyl and ropetyl chloride. Ta. In all these mixtures, the molar ratio of ethyl 20-butyl chloride ranges from 1:3 to 1=18.5. That is, the range is completely different from the 1:1 preferred in US Pat. No. 4,127,507. As can be seen from the experimental results, the yield of soluble alkylmagnesium was significantly increased by adding only a small amount of n-hexyl chloride (in the range of 5 to 13 mol%). I understand.

For example, in Example 5, the molar ratio of di-n-butyl and diethylmagnesium was 8=1, and even if an attempt was made to produce dialkylmagnesium, there was no addition of higher alkyl compounds, so only 5% of the soluble red sea bream cyano, alkyl I can only get it.

However, as shown in Example 6, only 5 mol%
By simply adding n-hexyl chloride to the reaction mixture, a hydrocarbon-soluble dialkylmagnesium composition having a very high Et, (90 mol%) of dilopithylmagnesium was produced in high yield. I was able to get it.

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316

Claims (1)

[Scope of Claims] 1. At least two lower dialkylmagnesium compounds whose alkyl groups are straight chain alkyls each having c and z 4, and at least one higher dialkyl magnesium compound whose alkyl groups are each a straight chain alkyl having C3 to 2o. A composition soluble in a hydrocarbon solvent containing a magnesium compound. 2. The composition according to claim 1, wherein the alkyl groups of the higher dialkylmagnesium compound are C2 to C2 alkyl groups, respectively. The composition according to claim 1, which contains two types of lower sialgyl magnesium compounds having 301 to 4 alkyl groups and C5 to 2ql4 di-n-amylmagnesium. 5. The composition of claim 1 containing di-11-hexylmagnesium. 6. The composition of claim 1 containing diethylmagnesium and di-n-butylmagnesium. 7. The composition of claim 6 containing di-n-hexylmagnesium. 4. The composition of claim 3, wherein the 82 lower dialkylmagnesium compounds differ by one carbon number in their alkyl groups. 9. The composition of claim 8 containing dimethylmagnesium and diethylmagnesium. 10 Claim 1 containing about 75 to 95 mol% lower dialkylmagnesium and about 5 to 25 mol% of one or more higher dialkylmagnesium compounds
composition of the term. 11 About 75-95 mol% lower sialicyl mag. 3. The composition of claim 2 containing a nesium compound and about 5 to 25 mole percent of a higher dialkylmagnesium compound. 12 about 70-93 mol% of the first lower dialkylmagnesium compound, about 2-20 mol% of the second lower dialkylmagnesium compound, and C6-3. A higher dialkylmagnesium compound having an alkyl group of about 5 to 2
The composition of claim 3 containing 5 mol%. 13 about 70-90 mol% of the first lower dialkylmagnesium compound, about 5-20 mol% of the second lower dialkylmagnesium compound, and C3-1. A higher dialkylmagnesium compound having an alkyl group of about 5 to 2
13. The composition of claim 12 containing 5 mol%. 14. A method of producing a hydrocarbon solution of a dialkylmagnesium compound composition comprising: ta) magnesium metal in the presence of a hydrocarbon solvent;
C11~,. (b) Simultaneously with step (a) or subsequently, reacting with an argyl halide having a straight-chain alkyl group;
reacting with an alkyl halide having 1 to 4 straight-chain alkyl groups: (C) Simultaneously or subsequently to step (a) and/or Φ), further with magnesium metal and a second alkyl halide having C1-4 straight-chain alkyl groups; reacting with an alkyl halide to form a mixture of a hydrocarbon solution of the dialkylmagnesium compound and undissolved solids; and (d) separating the hydrocarbon solution from the undissolved solids, throughout all steps in the absence of both moisture and oxygen. conduct. 15. The method of claim 14, wherein the hydrocarbon solvent is selected from the group consisting of C1-2o aliphatic, alicyclic and aromatic hydrocarbons. 16 Claims in which the alkyl halide is an alkyl chloride! Manufacturing method according to Section 14. 17. The method of claim 14 Jjj, wherein step (a) is carried out in the presence of a magnesium activator. 18 stages (a8 (b) and (C) are approximately 80-130
15. The manufacturing method according to claim 14, which is carried out at a temperature of °C. 19. The method of claim 14, wherein the ratio of the alkyl halide used in step (a) to the total amount of alkyl halide used in steps (1) and (C) is from about 1=18 to about I:3. Manufacturing method. 20 A composition comprising: (a) a first dialkylmagnesium compound having a C, ~4 straight chain alkyl group; (b) a C, ~4 straight chain alkyl group; a second dialkylmagnesium compound; tc) at least one dialkylmagnesium compound having a linear 1 alkyl group from C* to 2o; and (d) an aliphatic, IIW'j#t from Ch to
M, and a solvent selected from the group consisting of aromatic hydrocarbons. 2I The composition according to claim 20, wherein the alkyl group of component (C) is a C5-□2 straight-chain alkyl group. 22. The composition of claim 20, wherein components 1), (b) and (C) are in the following molar ratios: (a) about 70-93 mol%; (b) about 2-20 mol%;
and (07 about 5-25 mole %. Feather) The composition of claim 22JA, wherein components (a) 1. (t)) and (C) are in the following molar ratios: (a) about 70-90 moles %, (b) 5 to 20 mol % and (C) about 5 to 25 mol %. 24 Component <a> is di-n-butylmagnesium, component Φ is dienal magnesium, and component (C) is di-
Claim 20 which is n-hexylmagnesium
composition of the term.