US2744127A - Process for the manufacture of trialkylaluminium compounds - Google Patents
Process for the manufacture of trialkylaluminium compounds Download PDFInfo
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- US2744127A US2744127A US354626A US35462653A US2744127A US 2744127 A US2744127 A US 2744127A US 354626 A US354626 A US 354626A US 35462653 A US35462653 A US 35462653A US 2744127 A US2744127 A US 2744127A
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- aluminium
- magnesium
- reaction
- free
- ether
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- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 title description 4
- 239000004411 aluminium Substances 0.000 claims description 22
- 229910052782 aluminium Inorganic materials 0.000 claims description 22
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 21
- 239000011777 magnesium Substances 0.000 claims description 11
- 229910052749 magnesium Inorganic materials 0.000 claims description 10
- 150000001350 alkyl halides Chemical class 0.000 claims description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 8
- GANNOFFDYMSBSZ-UHFFFAOYSA-N [AlH3].[Mg] Chemical compound [AlH3].[Mg] GANNOFFDYMSBSZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910000838 Al alloy Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229910000861 Mg alloy Inorganic materials 0.000 description 5
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000005234 alkyl aluminium group Chemical group 0.000 description 2
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- -1 magnesium halide Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 2
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 241000985284 Leuciscus idus Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- JJSGABFIILQOEY-UHFFFAOYSA-M diethylalumanylium;bromide Chemical compound CC[Al](Br)CC JJSGABFIILQOEY-UHFFFAOYSA-M 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000000638 solvent extraction Methods 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/064—Aluminium compounds with C-aluminium linkage compounds with an Al-Halogen linkage
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
Definitions
- dialkylaluminium monohalides may be produced by the'action of alkyl halides on I an alloy of 70% aluminium and %'magnesium according to Grosse and Mavity, Journal of Organic Chemistry (1940), 5, 110 and 119. This'alloy contains aluminium and magnesium approximately in the molar ratio equation:
- magnesium-aluminiumalloys having a composition in the region of 57-65% magnesium and 43-35% aluminium can, despite their high magnesium content, be reacted with alkyl halides in the absence of ether to yield only or mainly aluminium trialkyls.
- the alloys specified are extremely brittle and can, therefore, be powdered to a of 2:1, so that the reaction may be represented'bythe very fine dust without difiiculty. They are suitably added v in this form in the process of the invention.
- Patented - May 1, 1956 -.matic hydrocarbons but is best carried out direct with the alkyl halide in undiluted state.
- the first reaction products mostly still contain some halogen, e. g. the product from MgsAlz and ethyl bromide contains from 5 to 10%, and rarely up to 15 %,-of halogen which corresponds to a content-of about double this percentage of diethylaluminium bromide.
- This halogen contcnt may easily be removed by a further treatment with the very finely powdered aluminium-magnesium alloy at a temperature of ISO-170 C., whereupon pure, halogen-free aluminium trialkyls are obtained in high yields.
- Example 1 1.3' kg. of finely powdered aIuminium magnesium alloy containing 40% Aland 60% Mg are mixed with "1 kg. ethylbromide in a small vessel furnished with a powerful stirring mechanism and an effective reflux cooler. After stirring for l-2.-hours,commencement of the reaction may be hastened by the addition of iodine or-rsome aluminium bromide or "ethylaluminiumsesquibromide"re-' action takes place with self-heating. A further'3.8 kg. of ethyl bromide is then added over a period of about 6 hours, intensive stirring being continued throughout. The stirring is continued so long as spontaneous reaction is noticeable (up to 24 hours). During this time the stirrer will occasionally stop.
- the mix may now be worked up by distilling oif the aluminium organic product which has formed.
- a distillate which consists mainly of triethylaluminium, but which also contains 7-15 of bromine. It is better to heat the vessel, after spontaneous reaction has ceased, for 20 hours at C. and then to distill. In this manner a halogenfree distillate may be obtained directly. Yield: 1.2-1.4 kg.
- Example 2 The procedure described in Example 1 is followed, but the reaction is carried out in a pressure-sealed reaction vessel, and instead of ethyl bromide a solution of 4 kg. of methyl bromide in 5 litres of hexane is used. After cessation of the spontaneous reaction, any of the following procedures may be followed: v
- Example 3 The procedure of Example 1 or 2 is followed, but three kg. of ethyl chloride are used instead of the 4.8 kg. of ethyl bromide.
- a pressure boiler suitable for use up to about atm. and furnished withv a pressure reflux condenser is employed, from the top of which the gases of the C2 series (ethylene, ethane), which accumulate in the vessel and cause a gradual inadmissible rise in pressure, are released from time to time. These gases are formed by secondary reactions.
- the whole further process is described in Example 1.
- Example 4 In the conversion described in this example, of 552 g. of butyl iodide with 75 g. of aluminium-magnesium alloy, the final reaction mixture consists of 420 g. of magnesium iodide and 200 g. of tributylaluminium. From this disparity between solid phase and liquid, difliculties may arise, which may be avoided by the following procedure.
- the cylinder jacket carries a portion of steel tube welded in as neck. About 75 g.
- the pot is mounted on a suitable rocking table and the neck connected with the necessary stationary fittings via a flexible metal tube.
- n-butyl iodide Whilst shaking continuously, 550 g. of n-butyl iodide are admitted to the pot at a speed which maintains the reaction temperature at about C. Following this, the temperature is maintained at this level for some time and is then raised to C.
- the tributylaluminium thus formed is easily extracted from the reaction mass by means of a hydrocarbon solvent (under nitrogen).
- Process for the production of aluminium trialkyls free from substantial quantities of halogen which comprises reacting an alkyl halide at a temperature between 30 and C. with a magnesium-aluminium alloy containing from 57 to 65% of magnesium and from 43 to 35% of aluminium in an ether-free reaction mixture and recovering the aluminium trialkyl thus formed.
- halogen-free aluminium trialkyl which comprises reacting an alkyl halide at a temperature between 30 and 170 C. with a magnesium aluminium alloy containing from 5 7 to 65% of magnesium and from 43 to 35% of aluminium in an ether-free reaction mixture, and thereafter treating the aluminium trialkyl thus formed with a finely divided magnesium-aluminium alloy of the composition specified above.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
PROCESS FOR THE 'MANUFACTURE F TRIALKYLALUMINIUM COMPOUNDS Karl Ziegler and Konrad Nagel, Mulheim an der Ruhr, Germany; saidNagel assignor to said Ziegler No Drawing. Application May 12, 1953,
' Serial No. 354,626
Claims priority, application Germany May 13, 1952 4 Claims. "(CL 260-448) This invention relates to the manufacture of trialkylaluminium compounds. ferred to as aluminium trialkyls.
It is known that the so-called alkylaluminium sesquihalides, i. e. mixtures of alkylaluminium dihalides and dialkylaluminium monohalides,.can be produced from me- These compounds are alsore- ,7
tallic aluminium and alkyl halides as exemplified by the following equation: I
2Al+ 3C2H5Cl=AlCl2C2H5 +AlCl( CzHs 2 Substantially homogeneous dialkylaluminium monohalides may be produced by the'action of alkyl halides on I an alloy of 70% aluminium and %'magnesium according to Grosse and Mavity, Journal of Organic Chemistry (1940), 5, 110 and 119. This'alloy contains aluminium and magnesium approximately in the molar ratio equation:
2A1 +Mg+4RHal=2AlR2Hal+MgHal2 The formation of the aluminium trialkyls would appear to require the use of an aluminium-magnesium alloy which corresponds at least to the composition AlzMgs. Nothing has hitherto become known of any attempts to carry out the reaction AlzMgs 6RHal=3MgHala+ 2AlRs conditions of the Grignard reaction i. e. in solution'in ether. (E. Krause and B. Wendt, Berichte de Deutschen Chemischen Gesellschaft, 56, 466 (1923). Ether-free aluminium trialkyls alone are not obtained in this manner, as the ether cannot be removed from the etherates by simple means. Thus the problem of producing ether-free aluminium trialkyls directly from alkyl halides and suitable aluminium alloys (which would follow the known formation of tetraethyllead from PbNa4 and 4 molecules of ethyl chloride) has hitherto remained unsolved. The ether-free aluminium trialkyls have recently become important as polymerisation catalysts for olefins.
It has now been found that magnesium-aluminiumalloys having a composition in the region of 57-65% magnesium and 43-35% aluminium (Mg3Al2 to MgzAl) can, despite their high magnesium content, be reacted with alkyl halides in the absence of ether to yield only or mainly aluminium trialkyls. The alloys specified are extremely brittle and can, therefore, be powdered to a of 2:1, so that the reaction may be represented'bythe very fine dust without difiiculty. They are suitably added v in this form in the process of the invention. In addition Patented -May 1, 1956 -.matic hydrocarbons, but is best carried out direct with the alkyl halide in undiluted state. In the latter case, though, the demand on the stirring mechanism which has to be provided .in the reaction vessel is fairly heavy, since the reaction products contain a large quantity of magnesium halide and accordingly easily form solid lumps so that a too weak stirrer sticks. This difficulty may be overcome by working in a rotating drum which contains grinding bodies. The aluminium organic compounds produced are recovered from the solid or semisolid reaction mixtures by distillation or solvent extraction.
The first reaction products mostly still contain some halogen, e. g. the product from MgsAlz and ethyl bromide contains from 5 to 10%, and rarely up to 15 %,-of halogen which corresponds to a content-of about double this percentage of diethylaluminium bromide. This halogen contcnt may easily be removed by a further treatment with the very finely powdered aluminium-magnesium alloy at a temperature of ISO-170 C., whereupon pure, halogen-free aluminium trialkyls are obtained in high yields.
Example 1 1.3' kg. of finely powdered aIuminium magnesium alloy containing 40% Aland 60% Mg are mixed with "1 kg. ethylbromide in a small vessel furnished with a powerful stirring mechanism and an effective reflux cooler. After stirring for l-2.-hours,commencement of the reaction may be hastened by the addition of iodine or-rsome aluminium bromide or "ethylaluminiumsesquibromide"re-' action takes place with self-heating. A further'3.8 kg. of ethyl bromide is then added over a period of about 6 hours, intensive stirring being continued throughout. The stirring is continued so long as spontaneous reaction is noticeable (up to 24 hours). During this time the stirrer will occasionally stop. The mix may now be worked up by distilling oif the aluminium organic product which has formed. In this case a distillate is obtained which consists mainly of triethylaluminium, but which also contains 7-15 of bromine. It is better to heat the vessel, after spontaneous reaction has ceased, for 20 hours at C. and then to distill. In this manner a halogenfree distillate may be obtained directly. Yield: 1.2-1.4 kg.
triethylaluminium or about 70-85% of the theoretical yield.
Example 2 The procedure described in Example 1 is followed, but the reaction is carried out in a pressure-sealed reaction vessel, and instead of ethyl bromide a solution of 4 kg. of methyl bromide in 5 litres of hexane is used. After cessation of the spontaneous reaction, any of the following procedures may be followed: v
(a) A further 5 litres of hexane is added to the reaction 60 vessel and the mixture is stirred. After allowing settle- Thereupon the trimethylaluminium is distilled off in vacuo. Yield: 60-75 of the theoretical yield.
(b) The hexane is distilled 0E and the residue heated as in Example 1 for 20 hours at 160 C. Following this, it is possible either to distill off the trimethylaluminium immediately in vacuo or-after cooling-to extract as described under (a) above, in this case conveniently with pentane.
(c) In. the presence of the originally used hexane, heating is carried out under pressure and agitation at 160 C., and the whole worked up according to (a) and (b).
Example 3 The procedure of Example 1 or 2 is followed, but three kg. of ethyl chloride are used instead of the 4.8 kg. of ethyl bromide. In each case a pressure boiler suitable for use up to about atm. and furnished withv a pressure reflux condenser is employed, from the top of which the gases of the C2 series (ethylene, ethane), which accumulate in the vessel and cause a gradual inadmissible rise in pressure, are released from time to time. These gases are formed by secondary reactions. The whole further process is described in Example 1.
Example 4 In the conversion described in this example, of 552 g. of butyl iodide with 75 g. of aluminium-magnesium alloy, the final reaction mixture consists of 420 g. of magnesium iodide and 200 g. of tributylaluminium. From this disparity between solid phase and liquid, difliculties may arise, which may be avoided by the following procedure. A stout-walled, completely Welded, cylindrical, steel pot of about three litres content (diameter of base=height of cylinder) serves as the reaction vessel. The cylinder jacket carries a portion of steel tube welded in as neck. About 75 g. of the aluminium-magnesium alloy (40:60) is introduced into the pot, which has previously been flushed out with nitrogen. Furthermore a number of grinding pellets, consisting conveniently of pieces of 6- edged steel of 10-15 mm. diameter and cut to length=width are also introduced. The pot is mounted on a suitable rocking table and the neck connected with the necessary stationary fittings via a flexible metal tube.
Whilst shaking continuously, 550 g. of n-butyl iodide are admitted to the pot at a speed which maintains the reaction temperature at about C. Following this, the temperature is maintained at this level for some time and is then raised to C.
The tributylaluminium thus formed is easily extracted from the reaction mass by means of a hydrocarbon solvent (under nitrogen).
We claim:
1. Process for the production of aluminium trialkyls free from substantial quantities of halogen which comprises reacting an alkyl halide at a temperature between 30 and C. with a magnesium-aluminium alloy containing from 57 to 65% of magnesium and from 43 to 35% of aluminium in an ether-free reaction mixture and recovering the aluminium trialkyl thus formed.
2. Process according to claim 1, which comprises rcacting an alkyl halide in the presence of an inert solvent, with a magnesium-aluminium alloy.
3. Process acccording to claim 2, in which said reaction is elfected with a hydrocarbon as a solvent.
4. Process for the production of halogen-free aluminium trialkyl, which comprises reacting an alkyl halide at a temperature between 30 and 170 C. with a magnesium aluminium alloy containing from 5 7 to 65% of magnesium and from 43 to 35% of aluminium in an ether-free reaction mixture, and thereafter treating the aluminium trialkyl thus formed with a finely divided magnesium-aluminium alloy of the composition specified above.
References Cited in the file of this patent Wendt: Ber., vol. 56, pages 466-472 (1923). Reid et al.: Chem. Soc. Jour. (1948) pages 1597 to 1601.
Grosse et al.: J. Org. Chem, vol. 5, page 110.
Claims (1)
1. PROCESS FOR THE PRODUCTION OF ALUMINIUM TRIALKYLS FREE FROM SUBSTANTIAL QUANTITIES OF HALOGEN WHICH COMPRISES REACTING AN ALKYL HALIDE AT A TEMPERATURE BETWEEN 30 AND 170* C. WITH A MAGNESIUM-ALUMINIUM ALLOY CONTAINING FROM 57 TO 65% OF MAGNESIUM AND FROM 43 TO 35% OF ALUMINIUM IN AN ETHER-FREE REACTION MIXTURE AND RECOVERING THE ALUMINIUM TRIALKYLTHUS FORMED.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE767400X | 1952-05-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2744127A true US2744127A (en) | 1956-05-01 |
Family
ID=6673529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US354626A Expired - Lifetime US2744127A (en) | 1952-05-13 | 1953-05-12 | Process for the manufacture of trialkylaluminium compounds |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2744127A (en) |
| GB (1) | GB767400A (en) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2863894A (en) * | 1954-01-22 | 1958-12-09 | Ici Ltd | Production of aluminium alkyls |
| US2903469A (en) * | 1956-07-26 | 1959-09-08 | Distillers Co Yeast Ltd | Chemical process |
| US2952698A (en) * | 1955-12-21 | 1960-09-13 | Exxon Research Engineering Co | Preparation of alkyl aluminum compounds |
| US3048612A (en) * | 1958-05-22 | 1962-08-07 | Goodrich Gulf Chem Inc | Transalkylation of aluminum alkyls |
| US3082232A (en) * | 1955-11-28 | 1963-03-19 | Phillips Petroleum Co | Preparation of organometallic monohalides |
| US3207770A (en) * | 1955-04-01 | 1965-09-21 | Ziegler | Production of alkyl aluminum compounds |
| US4118409A (en) * | 1974-03-27 | 1978-10-03 | Texas Alkyls, Inc. | Process for the simultaneous production of trimethylaluminum and alkylaluminum halides |
| US4349483A (en) * | 1980-12-29 | 1982-09-14 | Gulf Research & Development Company | Process for the preparation of aluminum trihydrocarbyls |
| US4364874A (en) * | 1981-07-13 | 1982-12-21 | Ethyl Corporation | Method of making aluminum alkyls |
| US4364873A (en) * | 1981-07-13 | 1982-12-21 | Ethyl Corporation | Method of making aluminum alkyls |
| US4364872A (en) * | 1981-07-13 | 1982-12-21 | Ethyl Corporation | Method of making aluminum alkyls |
| US4797500A (en) * | 1985-12-03 | 1989-01-10 | Sumitomo Chemical Company, Ltd. | Purification of organometallic compounds |
| US5359116A (en) * | 1992-05-13 | 1994-10-25 | Witco Gmbh | Process for preparing trimethylaluminum by reducing methylaluminum chlorides with sodium using high shearing forces |
| US5380898A (en) * | 1992-04-22 | 1995-01-10 | Hoechst Aktiengesellschaft | Process for preparing trimethylaluminum by reacting methylaluminum chlorides with sodium in solids reactors |
| WO1999003862A1 (en) * | 1997-07-18 | 1999-01-28 | Nippon Aluminum Alkyls, Ltd. | Process for producing trihydrocarbylaluminums |
| WO2018074231A1 (en) | 2016-10-20 | 2018-04-26 | 東ソー・ファインケム株式会社 | Aluminum alloy-containing composition, production method therefor, and trialkyl aluminum production method |
-
1953
- 1953-05-12 US US354626A patent/US2744127A/en not_active Expired - Lifetime
- 1953-05-12 GB GB13282/53A patent/GB767400A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2863894A (en) * | 1954-01-22 | 1958-12-09 | Ici Ltd | Production of aluminium alkyls |
| US3207770A (en) * | 1955-04-01 | 1965-09-21 | Ziegler | Production of alkyl aluminum compounds |
| US3082232A (en) * | 1955-11-28 | 1963-03-19 | Phillips Petroleum Co | Preparation of organometallic monohalides |
| US2952698A (en) * | 1955-12-21 | 1960-09-13 | Exxon Research Engineering Co | Preparation of alkyl aluminum compounds |
| US2903469A (en) * | 1956-07-26 | 1959-09-08 | Distillers Co Yeast Ltd | Chemical process |
| US3048612A (en) * | 1958-05-22 | 1962-08-07 | Goodrich Gulf Chem Inc | Transalkylation of aluminum alkyls |
| US4118409A (en) * | 1974-03-27 | 1978-10-03 | Texas Alkyls, Inc. | Process for the simultaneous production of trimethylaluminum and alkylaluminum halides |
| US4349483A (en) * | 1980-12-29 | 1982-09-14 | Gulf Research & Development Company | Process for the preparation of aluminum trihydrocarbyls |
| US4364872A (en) * | 1981-07-13 | 1982-12-21 | Ethyl Corporation | Method of making aluminum alkyls |
| US4364873A (en) * | 1981-07-13 | 1982-12-21 | Ethyl Corporation | Method of making aluminum alkyls |
| US4364874A (en) * | 1981-07-13 | 1982-12-21 | Ethyl Corporation | Method of making aluminum alkyls |
| US4797500A (en) * | 1985-12-03 | 1989-01-10 | Sumitomo Chemical Company, Ltd. | Purification of organometallic compounds |
| US5380898A (en) * | 1992-04-22 | 1995-01-10 | Hoechst Aktiengesellschaft | Process for preparing trimethylaluminum by reacting methylaluminum chlorides with sodium in solids reactors |
| US5359116A (en) * | 1992-05-13 | 1994-10-25 | Witco Gmbh | Process for preparing trimethylaluminum by reducing methylaluminum chlorides with sodium using high shearing forces |
| US6305622B1 (en) * | 1997-07-18 | 2001-10-23 | Nippon Aluminum Alkyls, Ltd. | Process for producing trihydrocarbyl aluminums |
| WO1999003862A1 (en) * | 1997-07-18 | 1999-01-28 | Nippon Aluminum Alkyls, Ltd. | Process for producing trihydrocarbylaluminums |
| JP4309478B2 (en) * | 1997-07-18 | 2009-08-05 | 日本アルキルアルミ株式会社 | Method for producing trihydrocarbyl aluminum |
| WO2018074231A1 (en) | 2016-10-20 | 2018-04-26 | 東ソー・ファインケム株式会社 | Aluminum alloy-containing composition, production method therefor, and trialkyl aluminum production method |
| KR20190072575A (en) | 2016-10-20 | 2019-06-25 | 토소 화인켐 가부시키가이샤 | COMPOSITION CONTAINING ALUMINUM ALLOY, METHOD FOR PRODUCING THE SAME, AND METHOD FOR PRODUCING TRIACEL ALUMINUM |
| US10870666B2 (en) | 2016-10-20 | 2020-12-22 | Tosoh Finechem Corporation | Aluminum alloy-containing composition, production method therefor, and trialkyl aluminum production method |
| EP3822279A1 (en) | 2016-10-20 | 2021-05-19 | Tosoh Finechem Corporation | Method for producing trialkylaluminum |
| KR20210123412A (en) | 2016-10-20 | 2021-10-13 | 토소 화인켐 가부시키가이샤 | Aluminum alloy containing composition, production method therefor, and trialkyl aluminum production method |
| US11591349B2 (en) * | 2016-10-20 | 2023-02-28 | Tosoh Finechem Corporation | Aluminum alloy-containing composition, production method therefor, and trialkyl aluminum production method |
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| Publication number | Publication date |
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| GB767400A (en) | 1957-02-06 |
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