DE1085515B - Process for the production of alkoxy or aryloxy aluminum hydrides or their complex salts with alkali hydrides - Google Patents
Process for the production of alkoxy or aryloxy aluminum hydrides or their complex salts with alkali hydridesInfo
- Publication number
- DE1085515B DE1085515B DEB51965A DEB0051965A DE1085515B DE 1085515 B DE1085515 B DE 1085515B DE B51965 A DEB51965 A DE B51965A DE B0051965 A DEB0051965 A DE B0051965A DE 1085515 B DE1085515 B DE 1085515B
- Authority
- DE
- Germany
- Prior art keywords
- hydrides
- alkoxy
- parts
- alkali
- tetrahydrofuran
- 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.)
- Pending
Links
- 239000003513 alkali Substances 0.000 title claims description 10
- -1 aryloxy aluminum hydrides Chemical class 0.000 title claims description 9
- 150000004678 hydrides Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 5
- 125000003545 alkoxy group Chemical group 0.000 title claims description 4
- 150000003839 salts Chemical class 0.000 title description 4
- 239000002904 solvent Substances 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- 239000011734 sodium Substances 0.000 description 9
- 235000002639 sodium chloride Nutrition 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 125000002481 alumanyl group Chemical group [H][Al]([H])[*] 0.000 description 2
- 229910000091 aluminium hydride Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 2
- 229910000103 lithium hydride Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- ZPAHTCCOPZRFCE-UHFFFAOYSA-K aluminum;dichloride;phenoxide Chemical compound Cl[Al](Cl)OC1=CC=CC=C1 ZPAHTCCOPZRFCE-UHFFFAOYSA-K 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 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
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- WQAJKGNQVZTJAE-UHFFFAOYSA-M chloro(diethoxy)alumane Chemical compound [Cl-].CCO[Al+]OCC WQAJKGNQVZTJAE-UHFFFAOYSA-M 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- NABPXHQIHROCQF-UHFFFAOYSA-N dibutoxyaluminum Chemical compound [Al+2].CCCC[O-].CCCC[O-] NABPXHQIHROCQF-UHFFFAOYSA-N 0.000 description 1
- NPEFICOHWIZPMC-UHFFFAOYSA-L dichloroalumanylium;ethanolate Chemical compound [Cl-].[Cl-].CCO[Al+2] NPEFICOHWIZPMC-UHFFFAOYSA-L 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- AUBCMGXPBMGRFT-UHFFFAOYSA-N octane;oxolane Chemical compound C1CCOC1.CCCCCCCC AUBCMGXPBMGRFT-UHFFFAOYSA-N 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011877 solvent mixture 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
- C07F5/069—Aluminium compounds without C-aluminium linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Alkoxy-oder Aryloxyaluminiumhydriden bzw. deren Komplexsalzen mit Alkalihydriden Es ist bekannt, Aluminiumchlorid bzw. -alkylchloride mit Lithiumhydrid oder auch mit Natriumhydrid umzusetzen. Die Umsetzungen mit Natriumhydrid verlaufen jedoch meist sehr träge und, wenn überhaupt, erst bei höherer Temperatur mit genügender Geschwindigkeit. Process for the preparation of alkoxy or aryloxy aluminum hydrides or their complex salts with alkali hydrides. It is known that aluminum chloride or -alkyl chlorides with lithium hydride or with sodium hydride to implement. The implementations with sodium hydride, however, they are usually very sluggish and, if at all, only contribute higher temperature with sufficient speed.
Dabei werden die Umsetzungsprodukte oft zersetzt. The reaction products are often decomposed in the process.
Es ist ferner bekannt, daß man durch Umsetzung eines Alkalimetalls und Wasserstoff oder eines Alkalihydnds mit einem Borsäuretrialkylester Alkalimetalltrialkoxyborhydride erhält. Diese Verbindungen enthaIten nur ein Wasserstoffatom je Atom Alkali, d. h., das Reduktionsvermögen je Komplexmolekül ist sehr gering. It is also known that by reacting an alkali metal and hydrogen or an alkali metal with a boric acid trialkyl ester alkali metal trialkoxyborohydride receives. These compounds contain only one hydrogen atom per atom of alkali, i.e. That is, the reducing power per complex molecule is very low.
Es wurde nun gefunden, daß man Aluminiumalkoxy-oder -aryloxyhydride bzw. deren Komplexsalze mit Alkalihydriden in einfacher Weise erhalten kann, wenn man Aluminiumalkoxy- bzw. Aluminiumaryloxyhalogenide mit Alkalihydriden in Gegenwart von indifferenten Lösungsmitteln, gegebenenfalls unter Druck, umsetzt. Je nach den für die Umsetzung verwendeten Mengen der Reaktionspartner erhält man entweder das Aluminiumalkoxyhydrid oder dessen Komplexsalz mit dem Alkalihydrid. Die Umsetzungen verlaufen nach den Gleichungen: Al(OR)nX3n + (3-n)MeH Al(OR)nX3n + (3-n + 1)MeH H wobei X ein Halogen, z.B. Chlor, Brom oder Jod, und Me ein Alkalimetall, z. B. Natrium, bedeutet und n = 1 oder 2 ist. Auch Sesquiverbindungen, z. B. Al2Cl8(O C2H5)3 kann man in dieser Weise zu Aluminiumalkoxy- oder -aryloxyhydriden umsetzen. It has now been found that aluminum alkoxy- or -aryloxyhydrides can be used or their complex salts with alkali hydrides can be obtained in a simple manner if one aluminum alkoxy or aluminum aryloxy halides with alkali hydrides in the presence of inert solvents, optionally under pressure. Depending on the The quantities of reactants used for the reaction are obtained either Aluminum alkoxy hydride or its complex salt with the alkali hydride. The implementations run according to the equations: Al (OR) nX3n + (3-n) MeH Al (OR) nX3n + (3-n + 1) MeH H where X is a halogen, e.g., chlorine, bromine or iodine, and Me is an alkali metal, e.g. B. Sodium, and n = 1 or 2. Sesqui compounds, e.g. B. Al2Cl8 (O C2H5) 3 can be converted in this way to aluminum alkoxy or aryloxy hydrides.
Man führt diese Umsetzungen in Gegenwart eines mdifferenten Lösungsmittels durch, weil Reaktionen in Lösungen im allgemeinen vollständiger und gleichmäßiger als zwischen festen Reaktionsteilnehmern ablaufen. Als besonders geeignete Lösungsmittel haben sich Äther, speziell Tetrahydrofuran, erwiesen. Die vorliegenden Reaktionen verlaufen, im Gegensatz zu vielen anderen Umsetzungen mit Alkalihydriden, bereits bei niedrigen Temperaturen, z. B. bei Raumtemperatur, mit guter Geschwindigkeit. Deshalb ist eine Zersetzung der Verfahrensprodukte praktisch ausgeschlossen. Die Umsetzung kann bei normalem oder erhöhtem Druck durchgeführt werden. These reactions are carried out in the presence of a different solvent because reactions in solutions are generally more complete and uniform than occur between solid reactants. As a particularly suitable solvent ethers, especially tetrahydrofuran, have been found. The present reactions In contrast to many other reactions with alkali hydrides, already proceeding at low temperatures, e.g. B. at room temperature, at good speed. Decomposition of the process products is therefore practically impossible. the Reaction can be carried out at normal or elevated pressure.
Die Umsetzungsprodukte sind ausgezeichnete Reduktionsmittel, die im Gegensatz zu den gebräuchlichen Alkalialuminiumhydriden wesentlich ungefährlicher in der Handhabung sind. Wahrscheinlich infolge einer oder mehrerer OR-Gruppen im Molekül sind die Umsetzungsprodukte auch in Lösungsmitteln oder Lösungsmittelgemischen überwiegend unpolarer Natur, wie Tetrahydrofuran-Oktan-Gemisch 10: 90, genügend löslich. The reaction products are excellent reducing agents that In contrast to the common alkali aluminum hydrides, it is much safer are in the handling. Probably as a result of one or more OR groups in the Molecules are the reaction products also in solvents or solvent mixtures predominantly non-polar nature, such as tetrahydrofuran-octane mixture 10:90, sufficient soluble.
Die in den Beispielen genannten Teile sind Gewichtsteile. The parts mentioned in the examples are parts by weight.
Al (OR)n H2 + (3 - n) Me C1 (1) Me [A1 (OR)n H3~"+ 1] + (3n) Me C1 (2) Beispiel 1 143 Teile Äthoxyaluminiumdichlorid, die in etwa 600 Teilen wasserfreiem Tetrahydrofuran gelöst sind, werden portionsweise innerhalb von 10 Minuten zu 72 Teilen Natriumhydrid hinzugefügt, die sich in einem Rührgefäß befinden. Die Umsetzung ist bei einer Temperatur von 40"C nach etwa 20 Minuten beendet. Die dabei entstehende Wärme wird durch Außenkühlung mit einem Gemisch aus festem Kohlendioxyd und Schwerbenzin abgeführt. Man erhält 98 Teile des Komplexes Na [AlH3(OC2H5)], die im Tetrahydrofuran gelöst sind, und 117 Teile Kochsalz, die im Tetrahydrofuran unlöslich sind.Al (OR) n H2 + (3-n) Me C1 (1) Me [A1 (OR) n H3 ~ "+ 1] + (3n) Me C1 (2) Example 1 143 parts of ethoxyaluminum dichloride, which is anhydrous in about 600 parts Tetrahydrofuran are dissolved, are added in portions within 10 minutes to 72 Parts of sodium hydride added, which are in a stirred vessel. The implementation is finished after about 20 minutes at a temperature of 40 ° C. The resulting Heat is generated by external cooling with a mixture of solid carbon dioxide and heavy fuel discharged. 98 parts of the complex Na [AlH3 (OC2H5)] are obtained in the tetrahydrofuran are dissolved, and 117 parts of common salt, which are insoluble in tetrahydrofuran.
Die Lösung kann, gegebenenfalls nachdem man das Kochsalz abgetrennt hat, direkt als Reduktionslösung verwendet werden. Man kann aber auch nach dem Abdestillieren des Lösungsmittels, gegebenenfalls im Vakuum, den Komplex als weißes kristallines Pulver erhalten. Falls das Vorhandensein von Kochsalz nicht stört, kann man auf seine Abtrennung verzichten. The solution can, if appropriate after the common salt has been separated off can be used directly as a reducing solution. But you can also after distilling off of the solvent, optionally in vacuo, the complex as a white crystalline Powder received. If the presence of table salt does not bother you, you can click renounce its separation.
Beispiel 2 152,5 Teile Diäthoxyaluminiummonochlorid, die in etwa 800 Teilen wasserfreiem Tetrahydrofuran teilweise gelöst und teilweise suspendiert sind, werden, wie im Beispiel 1 beschrieben, mit 48 Teilen Natriumhydrid umgesetzt. Man erhält 142 Teile des Komplexes Na [AlH2(O C2H5), die im Tetrahydrofuran gelöst sind, und 78 Teile Kochsalz, die im Tetrahydrofuran unlöslich sind. Die Aufbereitung erfolgt, wie im Beispiel 1 beschrieben. Example 2 152.5 parts of diethoxyaluminum monochloride, which is approximately 800 parts of anhydrous tetrahydrofuran partially dissolved and partially suspended are, as described in Example 1, reacted with 48 parts of sodium hydride. 142 parts of the complex are obtained Na [AlH2 (O C2H5), which is found in tetrahydrofuran are dissolved, and 78 parts of common salt, which are insoluble in tetrahydrofuran. The preparation takes place as described in Example 1.
Beispiel 3 209 Teile Dibutoxyaluminiummonochlorid, die in etwa 600 Teilen wasserfreiem Tetrahydrofuran teilweise gelöst und teilweise suspendiert sind, werden, wie im Beispiel 1 beschrieben, mit 48 Teilen Natriumhydrid umgesetzt. Example 3 209 parts of dibutoxyaluminum monochloride, equivalent to about 600 Parts of anhydrous tetrahydrofuran are partially dissolved and partially suspended, are, as described in Example 1, reacted with 48 parts of sodium hydride.
Man erhält durch praktisch vollständige Umsetzung den Komplex Na [AlH2(O C4H9)2] (= 198 Teile), der im Tetrahydrofuran gelöst ist, und 78 Teile Kochsalz, die im Tetrahydrofuran unlöslich sind. Die Aufarbeitung erfolgt, wie im Beispiel 1 beschrieben. Die Analyse der kochsalzfreien Tetrahydrofuranlösung des Komplexes ergab ein Molverhältnis Na: Al: H (durch Wasser freigesetzt) = 0,92:1:1,72. Die Analyse des vom Lösungsmittel befreiten Komplexes ergab: Na = 10,7 0in; Al = 15,3 01o; H (durch Wasser freigesetzt) = 0,85 8501 An Stelle von Tetrahydrofuran kann man mit gleichem Erfolg Hexan oder Cyclohexan als Lösungsmittel verwenden.The complex Na [AlH2 (O C4H9) 2] (= 198 parts), which is dissolved in tetrahydrofuran, and 78 parts of common salt, which are insoluble in tetrahydrofuran. The work-up is carried out as in the example 1 described. Analysis of the salt-free tetrahydrofuran solution of the complex gave a molar ratio Na: Al: H (released by water) = 0.92: 1: 1.72. the Analysis of the complex freed from the solvent gave: Na = 10.7 0 in; Al = 15.3 01o; H (released by water) = 0.85 8501 Instead of tetrahydrofuran can you can use hexane or cyclohexane as solvents with equal success.
Beispiel 4 191 Teile Phenoxyaluminiumdichlorid, die in etwa 800 Teilen wasserfreiem Tetrahydrofuran teilweise gelöst und teilweise suspendiert sind, werden, wie im Beispiel 1 beschrieben, mit 72 Teilen Natriumhydrid umgesetzt. Example 4 191 parts of phenoxyaluminum dichloride equivalent to about 800 parts partially dissolved anhydrous tetrahydrofuran and are partially suspended, as described in Example 1, reacted with 72 parts of sodium hydride.
Man erhält durch praktisch vollständige Umsetzung 146 Teile des Komplexes Na[AlH3(OC6H5)], in Tetrahydrofuran gelöst, und 117 Teile Kochsalz, die im Tetrahydrofuran unlöslich sind. Die Aufarbeitung erfolgt, wie im Beispiel 1 beschrieben. Die Analyse der kochsalzfreien Tetrahydrofuranlösung des Komplexes ergab ein Molverhältnis Na: Al: H (durch Wasser freigesetzt) = 0,90: 1: 2,72. Die Analyse des vom Lösungsmittel befreiten Komplexes ergab: Na = 14,2 ovo; Al = 18,0 ovo; H (durch Wasser freigesetzt) = 1,78°/o. An Stelle von Natriumhydrid kann man mit gleichem Erfolg die entsprechende Menge Kaliumhydrid oder Lithiumhydrid verwenden.Practically complete conversion gives 146 parts of the complex Na [AlH3 (OC6H5)], dissolved in tetrahydrofuran, and 117 parts of sodium chloride, which are contained in tetrahydrofuran are insoluble. Work-up is carried out as described in Example 1. The analysis the salt-free tetrahydrofuran solution of the complex gave a molar ratio of Na: Al: H (released by water) = 0.90: 1: 2.72. The analysis of the solvent freed complex gave: Na = 14.2 ovo; Al = 18.0 ovo; H (released by water) = 1.78%. Instead of sodium hydride, you can use the corresponding one with the same success Use amount of potassium hydride or lithium hydride.
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB51965A DE1085515B (en) | 1959-02-03 | 1959-02-03 | Process for the production of alkoxy or aryloxy aluminum hydrides or their complex salts with alkali hydrides |
| FR817209A FR1246620A (en) | 1959-02-03 | 1960-02-01 | Aluminum alkoxy- or aryloxyhydrides, their complex salts with alkali metal hydrides and process for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB51965A DE1085515B (en) | 1959-02-03 | 1959-02-03 | Process for the production of alkoxy or aryloxy aluminum hydrides or their complex salts with alkali hydrides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1085515B true DE1085515B (en) | 1960-07-21 |
Family
ID=6969725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB51965A Pending DE1085515B (en) | 1959-02-03 | 1959-02-03 | Process for the production of alkoxy or aryloxy aluminum hydrides or their complex salts with alkali hydrides |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1085515B (en) |
| FR (1) | FR1246620A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1194835B (en) * | 1960-06-03 | 1965-06-16 | Continental Oil Co | Process for the preparation of dialkoxyaluminum hydrides |
| US3281443A (en) * | 1961-02-24 | 1966-10-25 | Continental Oil Co | Preparation and use of dialkoxyaluminum hydride reducing agents |
| US3318934A (en) * | 1961-06-30 | 1967-05-09 | Ziegler Karl | Tertiary alkoxy-aluminum dialkyls and their manufacture |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3435059A (en) * | 1966-05-31 | 1969-03-25 | Dow Chemical Co | Aluminum monohydride catecholate |
| US3524870A (en) * | 1967-12-08 | 1970-08-18 | Dow Chemical Co | Preparation of aluminum monohydride diethoxide |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1139473A (en) * | 1955-12-12 | 1957-07-01 | Callery Chemical Co | Process for preparing metal trialkoxyborohydrides |
| DE1025854B (en) * | 1956-11-28 | 1958-03-13 | Degussa | Process for the preparation of alkali trialkoxy borohydride |
-
1959
- 1959-02-03 DE DEB51965A patent/DE1085515B/en active Pending
-
1960
- 1960-02-01 FR FR817209A patent/FR1246620A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1139473A (en) * | 1955-12-12 | 1957-07-01 | Callery Chemical Co | Process for preparing metal trialkoxyborohydrides |
| DE1025854B (en) * | 1956-11-28 | 1958-03-13 | Degussa | Process for the preparation of alkali trialkoxy borohydride |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1194835B (en) * | 1960-06-03 | 1965-06-16 | Continental Oil Co | Process for the preparation of dialkoxyaluminum hydrides |
| US3281443A (en) * | 1961-02-24 | 1966-10-25 | Continental Oil Co | Preparation and use of dialkoxyaluminum hydride reducing agents |
| US3318934A (en) * | 1961-06-30 | 1967-05-09 | Ziegler Karl | Tertiary alkoxy-aluminum dialkyls and their manufacture |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1246620A (en) | 1960-11-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1085515B (en) | Process for the production of alkoxy or aryloxy aluminum hydrides or their complex salts with alkali hydrides | |
| CH422780A (en) | Process for the preparation of aryl magnesium chlorides | |
| DE1964619C3 (en) | Adiabatic process for the manufacture of N monosubstituted 2,4 dichloro 6 amino s tnazines | |
| DE1178061B (en) | Process for the production of tetraorgano lead compounds | |
| DE2538158C3 (en) | Process for the preparation of monochlorobenzoyl chloride | |
| DE1041498B (en) | Process for the preparation of alkyl aluminum dihalides | |
| DE888696C (en) | Process for the preparation of alkyl lead compounds | |
| DE69013977T2 (en) | Process for the production of vanadium arenes. | |
| DE2361988A1 (en) | PROCESS FOR THE PRODUCTION OF TRIALKYLALUMINUM COMPOUNDS | |
| DE1059450B (en) | Process for the preparation of alkyl aluminum sesquichlorides | |
| DE838743C (en) | Process for the production of sulfamide | |
| DE2429757C3 (en) | Process for the preparation of 3-hexyn-1-ol | |
| EP0111203A1 (en) | Process for the preparation of 1,2-dichloroethane | |
| DE1912138C (en) | Process for the preparation of triaryl lead halides | |
| DE1167343B (en) | Process for the production of lead hydrocarbons | |
| AT237630B (en) | Process for the preparation of aryl magnesium chlorides | |
| AT225707B (en) | Process for the preparation of arylimino-halocarbonic acid esters | |
| DE877605C (en) | Process for the production of acid amides by breaking down ª ‡ -substituted carboxylic acids | |
| AT162930B (en) | Process for the preparation of organosilicon halides | |
| DE2429757B2 (en) | METHOD OF PREPARING 3-HEXIN-1-OL | |
| DE1044777B (en) | Process for the production of phosphorus pentafluoride | |
| DE1038019B (en) | Process for the preparation of hydrogen boride compounds | |
| DE1953713C3 (en) | Process for the production of oxygen-containing organoaluminum compounds | |
| DE1113688B (en) | Process for the production of carbonyls of chromium, molybdenum or tungsten | |
| DE1044046B (en) | Process for the production of sulfur hexafluoride |