DE1038553B - Process for the production of silicon compounds which contain at least one hydrogen atom on silicon - Google Patents
Process for the production of silicon compounds which contain at least one hydrogen atom on siliconInfo
- Publication number
- DE1038553B DE1038553B DEK24046A DEK0024046A DE1038553B DE 1038553 B DE1038553 B DE 1038553B DE K24046 A DEK24046 A DE K24046A DE K0024046 A DEK0024046 A DE K0024046A DE 1038553 B DE1038553 B DE 1038553B
- Authority
- DE
- Germany
- Prior art keywords
- silicon
- hydrogen atom
- contain
- production
- compounds
- 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
- 229910052710 silicon Inorganic materials 0.000 title claims description 8
- 239000010703 silicon Substances 0.000 title claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 title claims description 5
- 150000003377 silicon compounds Chemical class 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 150000002222 fluorine compounds Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005234 alkyl aluminium group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- -1 dibutyl Chemical group 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 230000000378 dietary effect Effects 0.000 description 3
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 2
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 2
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 1
- 101100004392 Arabidopsis thaliana BHLH147 gene Proteins 0.000 description 1
- ZBIZOWVIAHZPGQ-UHFFFAOYSA-N C(C(C)C)[AlH]CC(C)C.C(C)[AlH]CC Chemical compound C(C(C)C)[AlH]CC(C)C.C(C)[AlH]CC ZBIZOWVIAHZPGQ-UHFFFAOYSA-N 0.000 description 1
- 229910004014 SiF4 Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- XMIJDTGORVPYLW-UHFFFAOYSA-N [SiH2] Chemical compound [SiH2] XMIJDTGORVPYLW-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- DKCBXBIBYSLFNE-UHFFFAOYSA-N bis(3-methylbutyl)alumane Chemical compound C(CC(C)C)[AlH]CCC(C)C DKCBXBIBYSLFNE-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- ZMAPKOCENOWQRE-UHFFFAOYSA-N diethoxy(diethyl)silane Chemical compound CCO[Si](CC)(CC)OCC ZMAPKOCENOWQRE-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UCXUKTLCVSGCNR-UHFFFAOYSA-N diethylsilane Chemical compound CC[SiH2]CC UCXUKTLCVSGCNR-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052990 silicon hydride Inorganic materials 0.000 description 1
- ABTOQLMXBSRXSM-UHFFFAOYSA-N silicon tetrafluoride Chemical compound F[Si](F)(F)F ABTOQLMXBSRXSM-UHFFFAOYSA-N 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- QVMRVWAOMIXFFW-UHFFFAOYSA-N triethyl(fluoro)silane Chemical compound CC[Si](F)(CC)CC QVMRVWAOMIXFFW-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0896—Compounds with a Si-H linkage
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
- C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
- C07F7/126—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving the formation of Si-Y linkages, where Y is not a carbon or halogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Description
Verfahren zur Herstellung von Siliciumverbindungen, die zumindest ein Wasserstoffatom am Silicium enthalten Es wurde gefunden, daß Siliciumverbindungen, die zumindest ein Wasserstoffatom am Silicium enthalten, dadurch hergestellt werden können, daß Alkylalumi.niumhydride mit den Halogeniden, vorzugsweise den Fluoriden oder Komplexfluoriden, oder den Alkoxyverbind.ungen des Siliciums, gegebenenfalls bei erhöhter Temperatur in Gegenwart von Lösungsmitteln und/oder unter Druck, umgesetzt werden.Process for the production of silicon compounds, which at least contain a hydrogen atom on silicon It has been found that silicon compounds which contain at least one hydrogen atom on silicon, are thereby produced can that Alkylalumi.niumhydride with the halides, preferably the fluorides or complex fluorides, or the alkoxy compounds of silicon, optionally at elevated temperature in the presence of solvents and / or under pressure, reacted will.
Die Umsetzungen verlaufen z. B. nach den folgenden Gleichungen:
Als erfindungsgemäß verwendbare Alky la1uminiumhydride haben sich besonders vorteilhaft erwiesen: Diäthyl-, Dipropyl-, Dibutyl-, Diisobutyl-, Diamyl-oder Diisoamylaluminiumhydrid bzw. deren ätherate oder auch Alkylhalogen- bzw. Alky lalkoxyalumi.niumhy.dride. Die Dialkylaluminiumhydride können beispielsweise durch thermische Zersetzung der entsprechenden Aluminiumtrialkyle unter Abspaltung von Olefinen gewonnen werden.Alkyl aluminum hydrides which can be used according to the invention have proven to be Proven to be particularly advantageous: diethyl, dipropyl, dibutyl, diisobutyl, diamyl or Diisoamylaluminium hydride or their etherate or also alkylhalogen or Alky lalkoxyalumi.niumhy.dride. The dialkyl aluminum hydrides can, for example, by thermal decomposition of the corresponding aluminum trialkyls are obtained with elimination of olefins.
Die Umsetzungen der Alky laluminiumhy dride können je nach den verwendeten Ausgangsprodukten bei normaler oder erhöhter Temperatur in Gegenwart oder Abwesenheit von Lösungs- oder Verdünnungsmitteln sowie mit oder ohne Druck vorgenommen werden.The reactions of the Alky laluminiumhy dride can depending on the used Starting products at normal or elevated temperature in the presence or absence by solvents or diluents and with or without pressure.
Die erfindungsgemäß hergestellten Siliciumverbindungen, die zumindest ein Wassierstoffatom am Silicium enthalten, können als Reduktionsmittel in der anorganisehen oder organischen Chemie, als Treibmittel, Brennstoffe oder zu anderen Zwecken Verwendung finden.The silicon compounds produced according to the invention, which at least a hydrogen atom on silicon can be used as a reducing agent in the inorganic or organic chemistry, as propellants, fuels or other uses Find.
Beispiel 1 Zu 74 Gewichtsteilen 80%igem Diäthylaluminiumhydrid (Rest Aluminiumtriäthyl), welches sich in einem stählernen Druckgefäß befand, wurden 55 Gewichtsteile Siliciumtetrafluorid gepreßt. Die Temperatur wurde innerhalb einer Stunde bis auf 260° C erhöht: sodann wurde das Reaktionsgemisch abdestilliert. Es wurden folgende Fraktionen erhalten: Fraktion 1: Kp. etwa -10 bis -2° C; Si F.C2 H5 Si H3 C2H5-Gemisch. Fraktion 2: Kp. 50 bis 63°C; SiFZ(CZH5)2 SiH2(C2H5)z Gemisch.Example 1 To 74 parts by weight of 80% diethylaluminum hydride (remainder Aluminum triethyl), which was in a steel pressure vessel, became 55 Parts by weight of silicon tetrafluoride pressed. The temperature was within a Hour increased to 260 ° C: then the reaction mixture was distilled off. It the following fractions were obtained: Fraction 1: boiling point about -10 to -2 ° C; Si F.C2 H5 Si H3 C2H5 mixture. Fraction 2: boiling point 50 to 63 ° C .; SiFZ (CZH5) 2 SiH2 (C2H5) z mixture.
Fraktion 3: Kp. 105 bis 112° C; Si F (C2 H5)3-S iH (C2H5)3-Gemisch.Fraction 3: bp 105 to 112 ° C; Si F (C2 H5) 3-S iH (C2H5) 3 mixture.
Der Rest (21,2%) war Siliciumtetraäthyl. Beispiel 2 Zu 19 Gewichtsteilen Diäthylaluminiumhydrid wurden bei Zimmertemperatur und normalem Druck 29,6 Gewichtsteile Triäthylfluorsilan unter Rühren zugetropft. Die Reaktion setzte unter Erwärmung sofort ein und war nach etwa einer Stunde beendet. Erzhalten wurden in quantitativer Ausbeute (25,6 Gewichtsteile) Triäthvlsi.lan neben Diäthvlaluminiumfluorid. Wurde an Stelle von Diäthvlaluminiumhydrid Diisobutylaluminiumhydrid genommen, so verlief die Reaktion gleichartig, und die Ausbeute war gleich gut.The remainder (21.2%) was silicon tetraethyl. Example 2 At 19 parts by weight Diethyl aluminum hydride became 29.6 parts by weight at room temperature and normal pressure Triethylfluorosilane was added dropwise with stirring. The reaction continued with warming on immediately and ended after about an hour. Received were in quantitative Yield (25.6 parts by weight) of dietary content in addition to dietary aluminum fluoride. Became taken diisobutylaluminum hydride instead of dietary aluminum hydride, so proceeded the reaction was similar and the yield was equally good.
Beispiel 3 Zu 19 Gewichtsteilen Diäthylaluminiumhydrid wurden 1-1,3 Gewic'hr-steile Dimethvldichlorsilan analog Beispiel 2 zugegeben. Die Reaktion fand auch hier unter Erwärmung Matt und lieferte in beinahe quantitativer Ausbeute ein Gemisch von Dimethvlsilan und Dimethylchlorsilan (etwa 80:200/0). Wurden an Stelle von Dimethyldichlorsilan Dimethyldiäthoxysilan, Diäthyldiäthoxysilan oder andere Alkylkieselsäureester einbesetzt, so verlief die Reaktion ebenfalls exotherm und ohne Anwendung von Druck in quantitativer Ausbeute (Bildung von Dimethylsilan bzw. Diäthylsilan), was auch der Fall war, wenn an Stelle von Diäthylaluminium'hydrid Diisobutylaluminiumhydrid genommen wurde. Wurden an Stelle von AlkylkieselsäuTeestern Kieselsäureester mit Diäthylaluminium'hydrid bzw. Diisobutylaluminiumhydrid umgesetzt, so erhielt man, ebenfalls ohne Anwendung von Druck, in exothsrmer Reaktion Siliciumwasserstoff Si H4 in über 80o/oiger Ausbeute.Example 3 To 19 parts by weight of diethylaluminum hydride, 1-1.3 Partly by weight dimethyl dichlorosilane analogously to Example 2 was added. The reaction took place also here matt under heating and delivered in an almost quantitative yield Mixture of dimethylsilane and dimethylchlorosilane (about 80: 200/0). Were in place of dimethyldichlorosilane, dimethyldiethoxysilane, diethyldiethoxysilane or others Alkyl silicic acid esters occupied, the reaction was also exothermic and without applying pressure in quantitative yield (formation of dimethylsilane resp. Diethylsilane), which was also the case when instead of diethylaluminum hydride Diisobutyl aluminum hydride was taken. Were used in place of alkyl silicic acid esters Silicic acid ester reacted with diethylaluminum hydride or diisobutylaluminum hydride, in this way, also without the application of pressure, silicon hydride was obtained in an exothermic reaction Si H4 in over 80% yield.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK24046A DE1038553B (en) | 1954-11-12 | 1954-11-12 | Process for the production of silicon compounds which contain at least one hydrogen atom on silicon |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK24046A DE1038553B (en) | 1954-11-12 | 1954-11-12 | Process for the production of silicon compounds which contain at least one hydrogen atom on silicon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1038553B true DE1038553B (en) | 1958-09-11 |
Family
ID=7216910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK24046A Pending DE1038553B (en) | 1954-11-12 | 1954-11-12 | Process for the production of silicon compounds which contain at least one hydrogen atom on silicon |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1038553B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1117577B (en) * | 1958-11-05 | 1961-11-23 | Kali Chemie Ag | Process for the production of organotin hydrides |
| NL6616009A (en) * | 1965-11-15 | 1967-05-16 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2473434A (en) * | 1946-06-27 | 1949-06-14 | Du Pont | Method for preparing hydrocarbometallic halides |
| DE888852C (en) * | 1950-06-09 | 1953-09-07 | Bayer Ag | Process for the preparation of organohalosilanes |
-
1954
- 1954-11-12 DE DEK24046A patent/DE1038553B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2473434A (en) * | 1946-06-27 | 1949-06-14 | Du Pont | Method for preparing hydrocarbometallic halides |
| DE888852C (en) * | 1950-06-09 | 1953-09-07 | Bayer Ag | Process for the preparation of organohalosilanes |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1117577B (en) * | 1958-11-05 | 1961-11-23 | Kali Chemie Ag | Process for the production of organotin hydrides |
| NL6616009A (en) * | 1965-11-15 | 1967-05-16 |
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