US2931820A - Production of aluminium alkyls - Google Patents
Production of aluminium alkyls Download PDFInfo
- Publication number
- US2931820A US2931820A US735684A US73568458A US2931820A US 2931820 A US2931820 A US 2931820A US 735684 A US735684 A US 735684A US 73568458 A US73568458 A US 73568458A US 2931820 A US2931820 A US 2931820A
- Authority
- US
- United States
- Prior art keywords
- aluminium
- alkyl
- iodide
- reacting
- bromide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229910052782 aluminium Inorganic materials 0.000 title claims description 49
- 239000004411 aluminium Substances 0.000 title claims description 47
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 29
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 150000005375 primary alkyl halides Chemical class 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 150000001340 alkali metals Chemical class 0.000 claims description 9
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 7
- 229960003750 ethyl chloride Drugs 0.000 claims description 7
- 239000012442 inert solvent Substances 0.000 claims description 6
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 4
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 claims description 3
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 3
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims description 3
- 229940102396 methyl bromide Drugs 0.000 claims description 3
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 claims description 2
- BTUGGGLMQBJCBN-UHFFFAOYSA-N 1-iodo-2-methylpropane Chemical compound CC(C)CI BTUGGGLMQBJCBN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 claims description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 claims description 2
- 235000010210 aluminium Nutrition 0.000 description 39
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000005234 alkyl aluminium group Chemical group 0.000 description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 229910001508 alkali metal halide Inorganic materials 0.000 description 3
- 150000008045 alkali metal halides Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001348 alkyl chlorides Chemical class 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- -1 saturated alicyclic hydrocarbon Chemical class 0.000 description 2
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 2
- 229910000799 K alloy Inorganic materials 0.000 description 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- 229910000528 Na alloy Inorganic materials 0.000 description 1
- 229910000573 alkali metal alloy Inorganic materials 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 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
- 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
- C07F5/062—Al linked exclusively to C
Definitions
- This invention relates to the production of aluminium alkyls.
- British patent specification No. 762,200 describes a process for the production of an aluminium alkyl which comprises a-first step of reacting aluminium with at least one primary alkyl halide in the presence of an inert solvent to form a sesquihalide and a second step of reacting the sesquihalide with an alkali metal in the presence'of an'in'ert solvent toform the desired aluminium alkyl.
- the first step is carried out at a temperature not exceeding 50 C. and that the second step is carried out at a temperature within the range 100 to 180 C.
- the final reaction product of the above process consists of a Solution of an aluminium alkyl and insoluble material comprising finely divided aluminium and an alkali metal halide.
- the solution and the insoluble material are separated and the insoluble material may then be recycled to the first step of the process and the aluminium it contains reacted with further quantities of the primary alkyl halide.
- the alkali metal halide introduced in this way into the first step of the process may be separated from the sesquihalide solution by filtration.
- an aluminium alkyl by reacting aluminium with a primary alkyl halide in the pres ence of an inert solvent and then reacting the solution of halide as hereinafter defined to form an alkyl aluminium sesquihalide and then reacting this alkyl aluminiums'es quihalide in situ with an alkali metal to give a second reaction product containing additional quantities of the aluminium alkyl.
- the second reaction product' will also contain aluminium formed in the dehalogenation of the sesquihalide.
- the process of the iIIVEHlIlOH thCIC fore may be repeated a number of times to increase the conversion of aluminium into the aluminium alkyl. In; practice one repetition is sufiicient to give a high conver-' sion, for example about 87-88%, in a reasonable time.
- the solution of the aluminium alkyl in the inert solvent may be separated from insoluble matter by, for example, filtration. If de-' sired the aluminium alkyl may be' recovered by fractional distillation though this is often unnecessary.”
- Primary alkyl halides suitable for use in the process of the invention are defined as methyl chloride, bromide and iodide, ethyl chloride, bromide and iodide, propyl bromide and iodide, n-butyl bromide and iodide and isobutyl iodide.
- the process is of particular value in the production of aluminium trimethyl and aluminium triethyl using methyl chloride or ethyl chloride respectively as the primary alkyl halide.
- the temperature at which the process of the invention is conducted may be between 0 C. and 250 C. It is preferred that the temperature is within the range 50 C to 150 C. for example between 130 C. and 140 C.
- Solvents suitable for use in the process are those which dissolve the organic reactants and organic products and which are inert under the reaction conditions employed.
- the primary alkyl halide is gaseous at normal temperatures and pressures it is particularly desirable that it should be easily soluble in the solvent.
- the solvent should be free from aromatic compounds especially in the formation of the sesquihalide. It is preferred that the solvent is a parafiinic or saturated alicyclic hydrocarbon.
- Any alkali metal or alkali metal alloy may be used in the process of the invention. It is very convenient to use sodium or a sodium/ potassium alloy.
- Example 1.5 kg. ethyl bromide were added to a stirred suspension of 3.9 kg. aluminium powder in 15.8 kg. decalin contained in a closed reactor. After stirring for 1 hour the contents of the reactor were heated to C. and 13.8 kg. ethyl chloride added under pressure in 0.5 kg. portions at a rate sufficient to maintain the temperature at to C.
- the reactor was then vented through a condenser and molten sodium equivalent to the halogen present (determined by analysis) added at a rate sufficient to maintain the temperature at 130 to 140 C. After the addition of the sodium was complete the temperature was maintained for a further 3 hours. This completed the first stage of the process.
- the reaction product comprised precipitated aluminium and sodium chloride and a solution of aluminium triethyl.
- the reaction product was then cooled to 30 C. filtered and the filter cake washed three times with litres of decalin, the washings being added to the filtrate. This washing of the filter cake was repeated but the washings were now collected separately for use in the reaction of another batch of aluminium.
- the total reaction time of the process was 70 hours and the yield of aluminium triethyl was 12.5 kg. representing an overall yield of 90%. This yield was 75% greater than that obtained in the first stage of the process whereas the total reaction time was only 25% longer.
- a primary alkyl halide selected from the group consisting of methyl chloride, methyl bromide, methyl iodide, ethyl chloride, ethyl bromide, ethyl iodide, pro'pyl bromide, propyl iodide, n-butyl bromide, n-butyl iodide, isobutyl io'dide, to form an alkyl aluminium'sesquihalide and then reacting this alkyl aluminium sesquihalide in situ with an alkali metal to give a second reaction product containing additional quantities of the aluminium alkyl.
- a primary alkyl halide selected from the group consisting of methyl chloride, methyl bromide, methyl iodide, ethyl chloride, ethyl bromide, ethyl iodide, pro'pyl bromide, propyl iodide, n
- reaction product comprising aluminium is reacted to produce additional quantities of the aluminium alkyl at a temperature within the range 50 to C.
- inert solvent is a hydrocarbon selected from the group consisting of parafiinic and saturated alicyclic hydrocarbons.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
its:
PRODUCTION OF ALUMINIUM ALKYLS William Barclay and Peter Smith, Norton-on-Tees, England, assignors to Imperial Chemical Industries L mited, London, England, a corporation of Great Britain No Drawing. Application May 16, 1958 I Serial No. 735,684
This invention relates to the production of aluminium alkyls.
British patent specification No. 762,200 describes a process for the production of an aluminium alkyl which comprises a-first step of reacting aluminium with at least one primary alkyl halide in the presence of an inert solvent to form a sesquihalide and a second step of reacting the sesquihalide with an alkali metal in the presence'of an'in'ert solvent toform the desired aluminium alkyl.
In this process it is preferred that the first step is carried out at a temperature not exceeding 50 C. and that the second step is carried out at a temperature within the range 100 to 180 C.
The final reaction product of the above process consists of a Solution of an aluminium alkyl and insoluble material comprising finely divided aluminium and an alkali metal halide. The solution and the insoluble material are separated and the insoluble material may then be recycled to the first step of the process and the aluminium it contains reacted with further quantities of the primary alkyl halide. The alkali metal halide introduced in this way into the first step of the process may be separated from the sesquihalide solution by filtration.
Co-pending application U.S. Serial No. 714,948, filed February 13, 1958, describes a modification of the process of British patent specification No. 762,200 in which when the alkyl halide is an alkyl chloride, the reactio'n of the first step of the process is initiated by an alkyl bromide r iodide.
We have now found that the efiiciency of the above process can be considerably improved if the aluminium precipitated in the second step of the process is not separated from the solution of the aluminium alkyl and recycled to the first step of the process but is reacted in situ and in the absence of added aluminium, with a primary alkyl halide to form a sesquihalide which is then reacted with an alkali metal to give additional quantities of the aluminium alkyl.
In the absence of added aluminium the precipitated aluminium is converted into a sesquihalide rapidly and smoothly at temperatures of up to 250 C., no reaction initiator being necessary even when the primary alkyl halide is a primary alkyl chloride. As a result a high conversion of aluminium to aluminium alkyl can be achieved in a considerably less time than in the process of British patent specification No. 762,200. Further, since similar or the same temperatures can be used in the productio'n and dehalogenation of the sesquihalide much less cooling and reheating is required than in the recycle process of British patent specification 762,200. The filtration of alkali metal halide from the sesquihalide solution as described in British patent specification 762,200 is also eliminated.
According to the present invention there is provided a process for the production of an aluminium alkyl by reacting aluminium with a primary alkyl halide in the pres ence of an inert solvent and then reacting the solution of halide as hereinafter defined to form an alkyl aluminium sesquihalide and then reacting this alkyl aluminiums'es quihalide in situ with an alkali metal to give a second reaction product containing additional quantities of the aluminium alkyl.
It will .be appreciated that the second reaction product' will also contain aluminium formed in the dehalogenation of the sesquihalide. The process of the iIIVEHlIlOH thCIC fore, may be repeated a number of times to increase the conversion of aluminium into the aluminium alkyl. In; practice one repetition is sufiicient to give a high conver-' sion, for example about 87-88%, in a reasonable time.
After the completion of the process the solution of the aluminium alkyl in the inert solvent may be separated from insoluble matter by, for example, filtration. If de-' sired the aluminium alkyl may be' recovered by fractional distillation though this is often unnecessary."
Primary alkyl halides suitable for use in the process of the invention are defined as methyl chloride, bromide and iodide, ethyl chloride, bromide and iodide, propyl bromide and iodide, n-butyl bromide and iodide and isobutyl iodide.
The process is of particular value in the production of aluminium trimethyl and aluminium triethyl using methyl chloride or ethyl chloride respectively as the primary alkyl halide.
The temperature at which the process of the invention is conducted may be between 0 C. and 250 C. It is preferred that the temperature is within the range 50 C to 150 C. for example between 130 C. and 140 C.
Solvents suitable for use in the process are those which dissolve the organic reactants and organic products and which are inert under the reaction conditions employed. When the primary alkyl halide is gaseous at normal temperatures and pressures it is particularly desirable that it should be easily soluble in the solvent.
Preferably the solvent should be free from aromatic compounds especially in the formation of the sesquihalide. It is preferred that the solvent is a parafiinic or saturated alicyclic hydrocarbon.
Any alkali metal or alkali metal alloy may be used in the process of the invention. It is very convenient to use sodium or a sodium/ potassium alloy.
Air and moisture should be excluded from the apparatus in which the reaction is conducted.
Example 1.5 kg. ethyl bromide were added to a stirred suspension of 3.9 kg. aluminium powder in 15.8 kg. decalin contained in a closed reactor. After stirring for 1 hour the contents of the reactor were heated to C. and 13.8 kg. ethyl chloride added under pressure in 0.5 kg. portions at a rate sufficient to maintain the temperature at to C.
The reactor was then vented through a condenser and molten sodium equivalent to the halogen present (determined by analysis) added at a rate sufficient to maintain the temperature at 130 to 140 C. After the addition of the sodium was complete the temperature was maintained for a further 3 hours. This completed the first stage of the process. The reaction product comprised precipitated aluminium and sodium chloride and a solution of aluminium triethyl.
The reactor vent was then closed and 7.4 kg. ethyl chloride added under pressure at a rate suificient to main- Patented Apr. 5, 1 ,6
tain the temperature at 130 C. to 140 C. The reactor vent was then opened and molten sodium (50% of the weight previously used) added to the contents of the reactor at a rate sufficient to maintain the stated temperature which after the addition of sodium was completed, was maintained for a further 3 hours.
The procedure. described in the foregoing paragraph was then repeated using half the quantities of ethyl chloride and sodium stated in the said paragraph.
The reaction product was then cooled to 30 C. filtered and the filter cake washed three times with litres of decalin, the washings being added to the filtrate. This washing of the filter cake was repeated but the washings were now collected separately for use in the reaction of another batch of aluminium.
' The total reaction time of the process was 70 hours and the yield of aluminium triethyl was 12.5 kg. representing an overall yield of 90%. This yield was 75% greater than that obtained in the first stage of the process whereas the total reaction time was only 25% longer.
We claim:
1. In a process for the production of an aluminium alk'yl by reacting aluminium with a primary alkyl halide in the presence of an inert solvent and then reacting the solution of the alkyl aluminium sesquihalide thus formed with an alkali metal to give a reaction product comprising aluminium and a solution of an aluminium alkyl the step of reacting at a temperature above C. the said reaction product in the absence of added aluminium with a primary alkyl halide selected from the group consisting of methyl chloride, methyl bromide, methyl iodide, ethyl chloride, ethyl bromide, ethyl iodide, pro'pyl bromide, propyl iodide, n-butyl bromide, n-butyl iodide, isobutyl io'dide, to form an alkyl aluminium'sesquihalide and then reacting this alkyl aluminium sesquihalide in situ with an alkali metal to give a second reaction product containing additional quantities of the aluminium alkyl.
2. A process as claimed in claim 1 in which the reaction product comprising aluminium is reacted to produce additional quantities of the aluminium alkyl at a temperature within the range 50 to C.
3. A process as claimed in claim 1 in which the alkali metal is sodium.
4. A process as claimed in claim 1 in which the inert solvent is a hydrocarbon selected from the group consisting of parafiinic and saturated alicyclic hydrocarbons.
France Apr. 23, 1956 Belgium July 22, 1955
Claims (1)
1. IN A PROCESS FOR THE PRODUCTION OF AN ALUMINIUM ALKYL BY REACTING ALUMINUM WITH A PRMIARY ALKYL HALIDE IN THE PRESENCE OF AN INERT SOLVENT AND THEN REACTING THE SOLUTION OF THE ALKYL ALUMINIUM SESQUIHALIDE THUS FORMED WITH AN ALKALI METAL TO GIVE A REACTION PRODUCT COMPRISING ALUMINIUM AND A SOLUTION OF AN ALUMINIUM ALKYL THE STEP OF REACTING AT A TEMPERATURE ABOVE 50*C. THE SAID REACTION PRODUCT IN THE ABSENCE OF ADDED ALUMINIUM WITH A PRIMARY ALKYL HALIDE SELECTED FROM THE GROUP CONSISTING OF METHYL CHLORIDE, METHYL BROMIDE, METHYL IODIDE, ETHYL CHLORIDE, ETHYL BROMIDE, ETHYL IODIDE, PROPYL BROMIDE, PROPYL IODIDE, N-BUTYL BROMIDE, N-BUTYL IODIDE, ISOBUTYL IODIDE, TO FORM AN ALKYL ALUMINIUM SESQUIHALIDE AND THEN REACTING THIS ALKYL ALUMINIUM SESQUIHALIDE IN SITU WITH AND ALKALI METAL TO GIVE A SECOND REACTION PRODUCT CONTAINING ADDITIONAL QUANTITIES OF THE ALUMINIUM ALKYL.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17542/57A GB824428A (en) | 1957-06-03 | 1957-06-03 | Improvements in and relating to the production of aluminium alkyls |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2931820A true US2931820A (en) | 1960-04-05 |
Family
ID=10097008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US735684A Expired - Lifetime US2931820A (en) | 1957-06-03 | 1958-05-16 | Production of aluminium alkyls |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2931820A (en) |
| BE (1) | BE568231A (en) |
| DE (1) | DE1090662B (en) |
| FR (1) | FR1203066A (en) |
| GB (1) | GB824428A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3205260A (en) * | 1960-03-02 | 1965-09-07 | Montedison Spa | Process for the purification of terephthalic acid |
| US4118409A (en) * | 1974-03-27 | 1978-10-03 | Texas Alkyls, Inc. | Process for the simultaneous production of trimethylaluminum and alkylaluminum halides |
| US4364872A (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 |
| US4364873A (en) * | 1981-07-13 | 1982-12-21 | Ethyl Corporation | Method of making aluminum alkyls |
| US5618436A (en) * | 1996-02-16 | 1997-04-08 | Condea Vista Company | Process for clarifying metal alkyls |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE535085A (en) * | 1954-01-22 | 1900-01-01 |
-
0
- BE BE568231D patent/BE568231A/xx unknown
-
1957
- 1957-06-03 GB GB17542/57A patent/GB824428A/en not_active Expired
-
1958
- 1958-05-16 US US735684A patent/US2931820A/en not_active Expired - Lifetime
- 1958-06-03 FR FR1203066D patent/FR1203066A/en not_active Expired
- 1958-06-03 DE DEI14923A patent/DE1090662B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE535085A (en) * | 1954-01-22 | 1900-01-01 | ||
| FR1120572A (en) * | 1954-01-22 | 1956-07-09 | Ici Ltd | Aluminum-alkyl manufacturing |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3205260A (en) * | 1960-03-02 | 1965-09-07 | Montedison Spa | Process for the purification of terephthalic acid |
| US4118409A (en) * | 1974-03-27 | 1978-10-03 | Texas Alkyls, Inc. | Process for the simultaneous production of trimethylaluminum and alkylaluminum halides |
| US4364872A (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 |
| US4364873A (en) * | 1981-07-13 | 1982-12-21 | Ethyl Corporation | Method of making aluminum alkyls |
| US5618436A (en) * | 1996-02-16 | 1997-04-08 | Condea Vista Company | Process for clarifying metal alkyls |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1203066A (en) | 1960-01-15 |
| DE1090662B (en) | 1960-10-13 |
| GB824428A (en) | 1959-12-02 |
| BE568231A (en) | 1900-01-01 |
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