GB2047708A - Butyloctylmagnesium compounds - Google Patents
Butyloctylmagnesium compounds Download PDFInfo
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- GB2047708A GB2047708A GB8006076A GB8006076A GB2047708A GB 2047708 A GB2047708 A GB 2047708A GB 8006076 A GB8006076 A GB 8006076A GB 8006076 A GB8006076 A GB 8006076A GB 2047708 A GB2047708 A GB 2047708A
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- solution
- octyl
- butyl
- reaction
- compound
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- RGPSRYWDFHAWOT-UHFFFAOYSA-N CCCCCCCC[Mg]CCCC Chemical class CCCCCCCC[Mg]CCCC RGPSRYWDFHAWOT-UHFFFAOYSA-N 0.000 title description 2
- 239000011777 magnesium Substances 0.000 claims abstract description 64
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 56
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 10
- 150000004796 dialkyl magnesium compounds Chemical class 0.000 claims abstract description 10
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 10
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims abstract description 9
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 229930195733 hydrocarbon Natural products 0.000 claims description 13
- 150000002430 hydrocarbons Chemical class 0.000 claims description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims description 11
- -1 n-octyl radicals Chemical class 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 7
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 3
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract 1
- 125000002370 organoaluminium group Chemical group 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 description 17
- 238000001514 detection method Methods 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 238000000227 grinding Methods 0.000 description 4
- KXDANLFHGCWFRQ-UHFFFAOYSA-N magnesium;butane;octane Chemical group [Mg+2].CCC[CH2-].CCCCCCC[CH2-] KXDANLFHGCWFRQ-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 150000001348 alkyl chlorides Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001399 aluminium compounds Chemical class 0.000 description 1
- 229940077746 antacid containing aluminium compound Drugs 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides dialkyl magnesium compounds having n-butyl and n-octyl radicals, wherein the molar butyl : octyl ratio is from 1 : 1 to 9 : 1, and solutions of these compounds in hydrodcarbons. The compounds may be manufactured by reacting magnesium with butyl chloride and octyl chloride in the presence of an organoaluminium complex. They are useful as catalysts in polymerization reactions as they have a low crystallization tendency.
Description
SPECIFICATION
Butyloctylmagnesium compounds
Solutions of dialkylmagnesium compounds in hydrocarbons and the manufacture thereof are described in
British Patent Specifications 955806 and 1 003 551, and also in German Patent Specification 2 027 237. The dialkylmagnesium compounds are manufactured by reacting magnesium and alkyl halides in the presence of aluminium compounds. Dialkylmagnesium compounds soluble in hydrocarbons are dialkylmagnesium compounds that are complexed with alkylaluminium compounds, the aluminium content being determined by the quantity used.
The present invention provides a dialkylmagnesium compound having n-butyl and n-octyl radicals with a molar butyl . octyl ratio of from 1:1 to 9:1, preferably 3: 1, and a solution thereof in a hydrocarbon.
These are useful as catalysts and catalyst constituents fdr polymerisation, e.g. of ethylene, propylene or butadiene.
A dialkylmagnesium compound of the invention, especially as a solution thereof in a hydrocarbon, may be prepared by reacting magnesium with suitable butyl and octyl compounds, e.g. halides, preferably butyl chloride and octyl chloride, in the appropriate proportions in the presence of an organoaluminate complex.
Suitable organoaluminate complexes are, for example, those of the general formula
in which Ml represents a metal of the 1st main group of the Mendeleev Periodic Table, M" represents a metal of the 2nd main group of the Mendeleev Periodic Table,
R represents a straight-chain or branched alkyl radical having 1 to 18 carbon atoms,
X represents a halogeno radical or hydride radical, a represents the number 1 or 2, b represents a number from 1 to (3a + 1), c represents the number (3a + 1) d represents a number from 1 to 4, e represents the number (6 + 2d) - f, and frepresentsthe number 0,1 to 2, and if b ore > 1,the radicals represented by R can be the same or different.
The organoaluminate complex is preferably added to the reaction mixture before the reaction in an amount of from 0.25 to 2 mole %, more especially 0.3 to 1.3 mole %, calculated on the magnesium used.
Especially good results are achieved if the magnesium used for the reaction is magnesium powder ground in the presence of the complex. If a sufficient quantity of the complex compound is added to the magnesium before grinding it is unnecessary to make another addition of the complex compound before the reaction itself. It is thought that the grinding has no influence, however, on the type and composition of the butyl-octyl-magnesium compound produced or the solutions produced therefrom.
The reaction may be carried out in the presence of an inert solvent, for example a hydrocarbon, preferably a saturated hydrocarbon, for example hexane, heptane, methylcyclohexane or petroleum benzine fractions.
The solvent is used usually in an amount of 2 to 30 times the quantity by weight of the magnesium to be reacted.
The reaction is usually carried out under normal pressure. However, it is also possible to use higher or lower pressures. The reaction temperature is preferably within the range of 80 to 1 50 C, more especially 90 to 1200C, depending interalia on the solvent used.
Uniform dialkylmagnesium compounds and the previously known mixed alkylmagnesium compounds such as, for example, butyl-sec.-butyl-magnesium have a tendency to crystallise, which interferes with technical processes. In contrast, the butyl-octyl-magnesium of the invention has a very low crystallisation tendency. Thus, a 30% (by weight) solution of butyl-sec.-butyl-magnesium in hexane precipitates the dialkylmagnesium in the form of cyrstals which spontaneously ignite in the air. A solution of butyloctylmagnesium of the invention in a hydrocarbon, even in a saturated non-cyclic hydrocarbon, is distinguished by particular stability, reduced tendency towards spontaneous ignition, and a high capacity for taking up the material to be dissolved.
Precipitation of butyloctylmagnesium from hexane solutions is generally not observed even with dialkylmagnesium contents of clearly above 30% by weight.
The preparation of the compound of the invention may be carried out for example by the following general
procedure:
The solvent is placed under an inert gas atmosphere (for example argon or nitrogen) in a reaction vessel equipped with external heating, stirring, reflux cooler, thermometer and inlet device. The magnesium to be reacted is introduced, while stirring, and the chosen complex then added. (Using this procedure the solids do not become lumpy.) If grinding is to be carried out it is advisable to transfer the suspension to a mill, grind it
and then return it to the reaction vessel. After heating to at least 900C, the metered addition of the alkyl chlorides, for example as a mixture or, if desired, one after the other, is begun. The speed of the addition is dependent upon the scope of the heat supply.
After addition, the deposition of the solid portion can be accelerated, for example, by using a decanter or centrifuge; filtering is also suitable.
The following Examples illustrate the invention. Percentages given therein are percentages by weight.
Examples
Compounds of the invention were prepared by the above-described general procedure. Unless otherwise stated and heating before the alkyl chloride addition was carried out at 105 to 115 C. The alkyl chloride was metered in over approximately 2 hours, for safety reasons approximately 1 hour being allowed in addition for subsequent reaction. In the final step the deposition of solid was accelerated by centrifuging, and the solid was washed twice. The main solution and the-combined washing.solutions were tested according to known methods for their content of magnesium, chloride and foreign elements. The results are given in the
Table below.
The following abbreviations are used in the Table:
MS = main solution
WS = washing solutions
R2Mg yield = total yield of dialkylmagnesium, calculated on the magnesium used.
Et = ethyl
Bu = butyl
Oc = octyl
Example Substances used Reaction Products 1 1 mol Mg powder (smaller MS: 231 g
than 150u) 3.20 % Mg
0.75 mol butyl chloride 0.14 % Cl
0.25 mol octyl chloride 0.09 % Al
225 g i-nonane (boiling WS: 334g point range 115 - 140 C) 0.56% Mg
4.68 mmoi Mg4[Al28u120c2] 0.01 % Al
CI below detection limit
R2Mg Yield: 76 % th. yield Bu1.5Oc0.5Mg
Analysis:
71.68% C; 13.14% H;
13.91 % Mg; 0.87 % CI;
0.39 % Al 2 1 mol Mg chips (1 - 3 mm MS: 237 g x2mmx0.04mm) 3.19% Mg ground in 0.09 % Cl
225 g i-nonane 0.08% Al
with WS:280 g
4.68 mmol Mg4[Al2Bu12Oc2i 0.60 % Mg
ground product
reacted with 0.01 % Al
0.75 mol butyl chloride Cl below detection limit
and R2Mg yield:
0.25 mol octyl chloride 76 % th. yield Bu1.5Oc0.5Mg
Analysis: 71.89%C; 13.18%H; 14.10% Mg; 0.45% Cl;
0.38 % Al
Note: if Example 2 is carried
out without grinding,
the final solution contains
no active magnesium
Example Substances used Reaction Products 3 1 mol Mg powder (smaller MS: 224g than 150 ) 3.17 % Mg
0.5 mol octyl chloride 0.08% Cl
0.5 mol butyl chloride 0.09% Al
220 g i-nonane WS:315 g
4.68 mmol Mg[Al2Bu12Oc] 0.68 O/O Mg
below 0.01 % Al
Cl indetectable
R2Mg yield: 76 % th. yield BuOcMg
Analysis: 73.99%C; 12.93 % H;
12.37% Mg; 0.30% Cl;
0.35 % Al 4 as Example 3 but with MS: 232 9 0.20 mol octyl chloride 3.19% Mg
and 0.05% Cl
0.80 mol butyl chloride 0.08 % Al
WS: 321 g
0.57%Mg
0.01 %AI
0.01% Cl
R2Mg yield: 76 % th. yield Bu1.6Oc0.4Mg
Analysis:
71.72 % C; 13.19 % H;
15.08% Mg; 0.24% Cl;
0.36 % Al
Example Substances used Reaction products 5 1 mol Mg powder (smaller MS: 221 g
than 150 ) 3.27% Mg
0.75 mol butyl chloride 0.07 % CI
0.25 mol octyl chloride 0.08%
200 9 hexane WS: 290 9
4.68 mmol Mg4[Al2Bu12Oc2] 0.49 % Mg
in autoclave under pressure 0.01 % Al
maximum 2.8 atmospheres Cl not determined
gauge R2Mg yields:
71 % th. yield Bu1.5Oc0.5Mg
Analysis:
71.60% C; 13.17% H; 13.92 % Mg; 0.31 % Cl; 0.36%Al 6 1 mol Mg powder (smaller MS: 278 9
than 150 ) 2.60% Mg
0.75 mol butyl chloride 0.1% CI
0.25 mol octyl chloride 0.31 % Al
270 9 heptane WS: 280 g
20 mmol Mg4[Al2Bu12Oc2] 0.76 % Mg
Al and Cl not determined
R2Mg yield:
77 % th.yield Bu1.50c0.5Mg Analysis: 70.68 % C; 13.08 % H;
13.84% Mg; 0.56% Cl;
1.78 % Al
Example Substances used Reaction products 7 as Example 6 but with MS: 550 g
2.5 mmol Mg4[Al2Bu12Oc2] 1.37 % Mg
Afurther 270 g heptane 0.09% CI
were additionally added 0.02% Al
WS: 293 9 025% Mg Cl and Al below detection
limit
R2Mg yield: 68 % th. yield Bu1.5Oc0.5Mg
Analysis:
72.08%C; 13.18%H;
13.79%Mg; 0.78%Cl;
0.27 % Al 8 as Example 6 but with MS: 278 9
8.75 mmol Na(AIEt4) 2.59%Mg
0.1 %Cl 0.08%AI WS: 320 9 0.68%Mg
Al and Cl not determined
R2Mg yield:
77 % th. yield Bu1.5Oc0.5Mg
Analysis: 71.99%C; 13.12 % H;
13.82%Mg; 0.53%Cl;
0.11%Al 9 as Example 1 but with MS:230 g
4.38 mmol Mg2[AI2BugOc] 3.19 % Mg
as complex 0.09% Cl
0.09 % Al
WS: 290 g
0.61 % Mg
below 0.01 %Al
Cl below detection limit
R2Mg yield: 75 % th. yield Bu1.5Oc0.5Mg 10 as Example 1 but with MS: 229 g
4.37 mmol Mg[Al2Bu7Oc] 3.035%Mg
as complex 0.13% Cl
0.09 % Al
WS: 334g 0.65% Mg
0.01% AL
CI below detection limit
R2Mg yield: 72.5 % th. yield
11 as Example 1 but with MS: 240 g
4.38 mmol Mg2[Al2Et6Bu3Oc] 3.04 % Mg
as complex 0.11 %Cl
0.09 % Al
WS: 349 g
0.56% Mg
0.01 % Al
CI below detection limit
R2Mg yield:
76 % th. yield
Example Substances used Reaction products 12 as Example 1 but with MS:216g
8.75 mmol Na[AIH2Et21 3.03 % Mg
as complex and 0.09 % Cl
180 9 heptane as solvent 0.10%Al WS: 306 9
0.65% Mg
Al and Cl below detection
limit
R2Mg yield: 70.2 % th. yield
13 as Example 5 but with MS: 378 g
8.75 mmol Na(AlEt4) 1.60 % Mg
as complex 0.1 % Cl 0.08 % Al
WS: 3219
0.55%Mg
< 0.01 %AI
Cl below detection limit
R2Mg yield:
74 % th. yield
14 as Example 1 but with MS: 237 g
8.5 mmol Li(AlEt3Bu) 2.96% Mg
as complex 0.07% Cl
0.08% Al
WS: 286 9
0.69% Mg
0.01 % Al
Cl below detection limit
R2Mg yield: 74 % th. yield
15 as Example 1 but with MS:214g
4.375 mmol Na[Al2Et6F] 3.12 /0 Mg
as complex and 0.12% Cl
180 g n-octane as solvent 0.1 % Al
WS: 284 9
0.71 % Mg
Al and Cl below detection
limit
R2Mg yield:
71.4 % th. yield
16 as Example 1 but with MS: 231 9
8.75 mmol Li[Al(n-Oc)3n-Bul] 3.03 % Mg
as complex 0.09 % CI
0.09 % Al
WS: 309 9
0.65% Mg
0.01 % Al
Cl below detection limit
R2Mg yield:
74.1 % th. yield
Example Substances used Reaction products 17 as Example 1 but with MS: 235.5 9 8.75 mmol Na[AlEtCl3] 2.75 % Mg
as complex 0.11 %Cl
0.08 % Al
WS:357 g 0.56 % Mg
0.01 % Al
Cl below detection limit
R2Mg yield:
69.5 % th. yield 18 as Example 1 but with MS:250g
4.375 mmol Na[AIEt4] 2.80 % Mg
4.375 mmol Li[Al(n-Oc)3n-Bu] 0.1 % Cl
as complex mixture 0.09 % Al WS: 333 9
0.64% Mg Al and Cl below detection
limit
R2Mg yield: 75 % th. yield 19 as Example 1 but with MS: 234 g
4.3 mmol 3.09 % Mg
MG2[Al2(i-Bu)4(n-Bu)3OcH2] 0.11%Cl
as complex 0.08 % Al WS: 355 9 0.57 % Mg
0.01 %AI
Cl below detection limit
R2Mg yield: 76 % th. yield 20 as Example 1 but with MS: 210 g
4.37 mmol Ca(Al2Et8) 3.07 % Mg
as complex 0.09 % Cl 0.08% Al WS:310g
0.67 % Mg
Cl and Al below detection
limit
R2Mg yield:
70.1 %th.yield
Claims (22)
1. A dialkylmagnesium compound having n-butyl and n-octyl radicals, wherein the molar butyl : octyl ratio is from 1 : 1 to 9: 1.
2. A compound as claimed in claim 1, wherein the molar butyl : octyl ratio os 3 : 1.
3. A compound as claimed in claim 1, wherein the molar butyl : octyl ratio is 1 : 1.
4. A compound as claimed in claim 1, wherein the molar butyl : octyl ratio is 4 : 1.
5. A solution of a compound claimed in any one of claims 1 to 4 in a hydrocarbon.
6. A solution as claimed in claim 5, wherein the hydrocarbon is a saturated hydrocarbon.
7. A solution as claimed in claim 6, wherein the hydrocarbon is hexane, heptane, methylcyclohexane, a petroleum fraction, i-nonane or n-octane.
8. A solution as claimed in any one of claims 5 to 7, wherein the hydrocarbon is present in an amount of 2 to 30 times the weight of magesium in the compound.
9. A solution as claimed in any one of claims 5 to 7, which contains at least 30 % by weight of compound claimed in claim 1.
10. A solution of a dialkylmagnesium compound having n-butyl and n-octyl radicals, wherein the molar butyl : octyl ratio is from 1:1 to 9:1, in a hydrocarbon, manufactured by reacting magensium with butyl chloride and octyl chloride in the presence of an organoaluminate complex.
11. A solution as claimed in claim 10, wherein the organoaluminate complex has the general formula
in which Ml represents a metal of the 1st main group of the Mendeleev Periodic Table.
M" represents a metal of the 2nd main group of the Mendeleev Periodic Table.
R represents a straight-chain or branched alkyl radical having 1 to 18 carbon atoms.
D represents a halogeno radical or hydride radical.
a represents the number 1 or 2.
b represents a number from 1 to (3a + 1).
c represents the number (3a + 1) - b.
drepresentsa number from 1 to 4.
e represents the number (6 + 2d) - f, and frepresentsthe number 0,1 or 2.
and if b or e > 1,the radicals represented by R can be the same or different.
12. A solution as claimed in claim 10 or claim 11, wherein the organoaluminate complex is present in the reaction mixture in an amount of from 0.25 to 2 mole % calculated on the magnesium used.
13. A solution as claimed in claim 12, wherein the organoaluminate complex is present in the reaction mixture in an amount of from 0. to 1.3 mole % calculated on the magnesium used.
14. A solution as claimed in any one of claims 10 to 13, wherein the magnesium is ground with the complex before reaction.
15. A solution as claimed in any one of claims 10 to 14, wherein the reaction is carried out in a hydrocarbon solvent used in an amount 2 to 30 times the weight of magnesium to be reacted.
16. A solution as claimed in any one of claims 10 to 15, wherein the reaction is carried out in a saturated hydrocarbon solvent.
17. A solution as claimed in claim 16, wherein the hydrocarbon is hexane, heptane, methylcyclohexane, a petroleum fraction, i-nonane or n-octane.
18. A solution as claimed in any one of claims 10 to 17, wherein the reaction is carried out at a temperature in the range of from 80 to 150"C.
19. A solution as claimed in claim 18, wherein the reaction is carried out at a temperature in the range of from 90 to 120"C.
20. A solution as claimed in any one of claims 10 to 19, wherein the molar butyl : octyl ratio is 3:1.
21. A solution as claimed in claim 10, wherein the reaction is carried out substantially as described herein.
22. A solution as claimed in claim 10, wherein the reaction is carried out substantially as described in any one ofthe Examples 1 to 20 herein.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2907025 | 1979-02-23 | ||
| DE2943357A DE2943357C2 (en) | 1979-02-23 | 1979-10-12 | ETHER-FREE SOLUTIONS OF N-BUTYL-N-OCTYL-MAGNESIUM COMPOUNDS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2047708A true GB2047708A (en) | 1980-12-03 |
| GB2047708B GB2047708B (en) | 1983-02-02 |
Family
ID=25777935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8006076A Expired GB2047708B (en) | 1979-02-23 | 1980-02-22 | Butyloctyl-magnesium compounds |
Country Status (5)
| Country | Link |
|---|---|
| DE (1) | DE2943357C2 (en) |
| FR (1) | FR2449695B1 (en) |
| GB (1) | GB2047708B (en) |
| IT (1) | IT1209300B (en) |
| NL (1) | NL7909273A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3104791A1 (en) * | 1981-02-11 | 1982-09-02 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | ORGANIC BARIUM-MAGNESIUM COMPLEXES AND METHOD FOR THEIR PRODUCTION |
| EP0422686B1 (en) * | 1989-10-13 | 1997-04-16 | Fuji Photo Film Co., Ltd. | Image-forming material containing an aluminate complex |
| DE19757499A1 (en) * | 1997-12-23 | 1999-06-24 | Studiengesellschaft Kohle Mbh | High yield production of Grignard compounds, for production of organomagnesium compounds |
| EP4153602A1 (en) | 2020-05-20 | 2023-03-29 | LANXESS Organometallics GmbH | Novel organo-magnesium compounds and their use |
| EP4520722A1 (en) | 2023-09-05 | 2025-03-12 | LANXESS Organometallics GmbH | Sustainable ziegler-natta catalysts |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB955806A (en) * | 1959-04-29 | 1964-04-22 | Nat Res Dev | Preparation and use of organomagnesium materials |
| GB1003551A (en) * | 1960-12-01 | 1965-09-08 | Nat Res Dev | Organomagnesium materials |
| NL139981B (en) * | 1969-06-04 | 1973-10-15 | Stamicarbon | PROCESS FOR THE PREPARATION OF SOLUBLE COMPLEXES OF MAGNESIUM DIALKYLES AND ORGANO-ALUMINUM COMPOUNDS. |
| US4069267A (en) * | 1976-10-27 | 1978-01-17 | Lithium Corporation Of America | Stable diorganomagnesium compositions |
| US4127507A (en) * | 1977-06-29 | 1978-11-28 | Texas Alkyls, Inc. | Hydrocarbon soluble straight-chain di-(lower alkyl) magnesium compositions |
-
1979
- 1979-10-12 DE DE2943357A patent/DE2943357C2/en not_active Expired
- 1979-12-21 NL NL7909273A patent/NL7909273A/en active Search and Examination
-
1980
- 1980-01-18 IT IT8019286A patent/IT1209300B/en active
- 1980-02-22 FR FR808003904A patent/FR2449695B1/en not_active Expired
- 1980-02-22 GB GB8006076A patent/GB2047708B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT8019286A0 (en) | 1980-01-18 |
| FR2449695A1 (en) | 1980-09-19 |
| IT1209300B (en) | 1989-07-16 |
| DE2943357C2 (en) | 1982-11-11 |
| FR2449695B1 (en) | 1985-07-26 |
| NL7909273A (en) | 1980-08-26 |
| GB2047708B (en) | 1983-02-02 |
| DE2943357A1 (en) | 1980-09-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 732E | Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 20000221 |