DE1252683B - Verfahren zur Herstellung von Cyclodisilazanen - Google Patents

Verfahren zur Herstellung von Cyclodisilazanen

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Publication number
DE1252683B
DE1252683B DENDAT1252683D DE1252683DA DE1252683B DE 1252683 B DE1252683 B DE 1252683B DE NDAT1252683 D DENDAT1252683 D DE NDAT1252683D DE 1252683D A DE1252683D A DE 1252683DA DE 1252683 B DE1252683 B DE 1252683B
Authority
DE
Germany
Prior art keywords
general formula
carbon atoms
radical
atom
disilylamines
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
Application number
DENDAT1252683D
Other languages
English (en)
Inventor
Rüschlikon Zürich Dr. Chem Walter Fink (Schweiz)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Monsanto Co
Original Assignee
Monsanto Co
Priority date (The priority date 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 date listed.)
Publication date
Priority claimed from CH384062A external-priority patent/CH407114A/de
Priority claimed from CH327563A external-priority patent/CH460000A/de
Publication of DE1252683B publication Critical patent/DE1252683B/de
Pending legal-status Critical Current

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    • G—PHYSICS
    • G21—NUCLEAR PHYSICS; NUCLEAR ENGINEERING
    • G21F—PROTECTION AGAINST X-RADIATION, GAMMA RADIATION, CORPUSCULAR RADIATION OR PARTICLE BOMBARDMENT; TREATING RADIOACTIVELY CONTAMINATED MATERIAL; DECONTAMINATION ARRANGEMENTS THEREFOR
    • G21F1/00—Shielding characterised by the composition of the materials
    • G21F1/02—Selection of uniform shielding materials
    • G21F1/10—Organic substances; Dispersions in organic carriers
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    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/022—Boron compounds without C-boron linkages
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Description

BUNDESREPUBLIK DEUTSCHLAND
DEUTSCHES
PATENTAMT
AUSLEGESCHRIFT
1 252 Wo Int. Cl.:
C07d
C O 7 F 7/10
Deutsche Kl.: 12 ο - 26/03
1252JL
Nummer:
Aktenzeichen: M 60285 IV b/12 ο
Anmeldetag: 13. April 1964
Auslegetag:
r 1967
Gegenstand des Patentes 1 214 683 ist ein Verfahren zur Herstellung von heterocyclischen Viererringverbindungen der allgemeinen Formel
R2Si NR'
Verfahren zur Herstellung von Cyclodisilazanen
Zusatz zum Patent: 1 214 683
worin die Symbole die folgende Bedeutung besitzen: M = Silicium, Bor, Phosphor, O = P-Rest, S = P-Rest to oder Mg; R = gegebenenfalls halogenierter Alkyl-, Alkenyl-, Cycloalkyl-, Cycloalkenyl-, Aralkyl-, Aralkenyl- oder Arylrest mit bis zu 20 Kohlenstoffatomen, über Sauerstoff gebundener Rest eines einwertigen Alkohols oder Phenols mit bis zu 20 Kohlenstoffatomen, wobei zwei Reste am gleichen Silicium- bzw. M-Atom zusammengenommen eine cyclische Struktur bilden; R' = Alkyl-, Cycloalkyl-, Alkenyl-, Cycloalkenyl-, Aralkyl-, Aralkenyl-, Aryl- oder heterocyclischer Rest mit bis zu 20 Kohlenstoffatomen; R" = Halogenatom oder die Gruppe
— NR' — SiR2 — NR' — MR„
Anmelder:
Monsanto Company, St. Louis, Mo. (V. St. A.)
Vertreter:
Dr.-Ing. H. Ruschke und Dipl.-Ing. H. Agular,
Patentanwälte, München 27, Pienzenauer Str. 2
Als Erfinder benannt:
Dr. Chem. Walter Fink,
Rüschlikon, Zürich (Schweiz)
Beanspruchte Priorität:
Schweiz vom 15. März 1963 (3275)
die an ihrem anderen Ende den gleichen Viererring aufweist; η = Null oder ganze Zahl; ν = Valenz von M, wobei M, anstatt mit den Radikalen R und R" verbunden zu sein, auch Teil eines zweiten, identischen Viererringes sein kann, das dadurch gekennzeichnet ist, daß man ein Diaminodiorganosilan der allgemeinen Formel
R'NH — SiR2 — NHR'
worin R und R' die gleiche Bedeutung wie oben haben, in Form eines Dialkalisalzes oder Di-Grignard-Derivates, mit mindestens einer äquimolaren Menge eines Halogenids der allgemeinen Formel
Sauerstoffausschluß erhitzt, Die Erhitzung wird abgebrochen, wenn die Abspaltung der berechneten Menge Halogensilan praktisch beendet ist.
Die Herstellung der Disilylamine aus primären Aminen und Halogensilanen ist bekannt.
Nach dem vorliegenden Verfahren verläuft die Cyclisierung zum Viererring mit z. B. Bis-(dimethylchlorsilyl)-anilin nach der folgenden Gleichung:
Cl(CHa)2Si — N(C6H5) — Si(CHa)2Cl
C6H5N- Si(CHa)2
worin R und ν die gleiche Bedeutung wie oben haben, X ein Halogenatom und m mindestens 2 ist, in einem inerten Lösungs- oder Verdünnungsmittel umsetzt.
Tn weiterer Ausgestaltung des Verfahrens gemäß Patent 1 214 683 wurde nun gefunden, daß man zu den Cyclodisilazenen (Formel 1,M = Si) gelangt, wenn man Disilylamine der allgemeinen Formel
X3-„R„Si — N R' — SiR„X3_„
worin R, R', X und η die gleiche Bedeutung wie oben haben und mindestens ein X vorhanden ist, unter + 2Si(CHa)2Cl2
(CH3)2Si NC6H5
Die zweckmäßige Reaktionstemperatur liegt in der Regel im Bereich von etwa 100° C und der Siedetemperatur des Disilylamins. Das sich abspaltende Halogensilan wird vorzugsweise aus der Reaktionsmischung kontinuierlich entfernt. Die Leichtigkeit, mit welcher diese Reaktion abläuft, ist von der Festigkeit der Silicium-Stickstoff- und Silicium-Halogen-Bindungen abhängig. Die Cyclisierung verläuft besonders leicht, wenn an einem Siliciumatom, neben wenigstens einem für die Reaktion notwendigen Halogenatom, aliphatische Reste und am Stickstoffatom ein aromatischer Rest vorhanden sind.
709 609/465
Man kann die Herstellung der Disilylamine und deren Cyclisierung zu einem einzigen Verfahren kombinieren. Man kann beispielsweise ein Dialkalisalz eines primären Amins mit dem Halogensilan zum entsprechenden Disilylamin umsetzen und das letztere ohne vorherige Isolierung, nötigenfalls unter Druckanwendung, cyclisieren. In gleicher Weise kann man beispielsweise ein sekundäres Silylamin in Form eines Alkalisalzes mit dem Halogensilan umsetzen und anschließend cyclisieren.
Beispiel 1
Zu 29,8 g (0,18 Mol) Trimethylsilylanilin in 30 ml Xylol werden in einer Stickstoffatmosphäre unter Rühren 30 ml (0,18 Mol) einer 6n-Lösung von Butyllithium in Hexan zugetropft und die Mischung während einer Stunde auf 50 bis 60°C erwärmt. Die Suspension des Lithiumsalzes tropft man zu 23,2 g (0,18 Mol) Dimethylsiliciumdichlorid in 100 ml Xylol und kocht anschließend 5 Stunden. Die Umwandlung ist 100°/0ig, bezogen auf das isolierte Lithiumchlorid (7,63 g). Die abzentrifugierte Lösung wird vom Xylol befreit und der Rückstand (45,3 g) fraktioniert destilliert.
Ausbeute 39,8 g (86,0 °/0) unsymmetrisches Disilylamin der Formel
(CH3)3Si — N(C6H5) — Si(CH3)2Cl;
Kp.0>2 = 71 bis 720C; n%° 1,4977.
Molgewicht:
Berechnet
gefunden
257,0;
257,0.
gegeben. Nachdem die Mischung 5 Stunden zum Rückfluß (etwa 140° C) erhitzt worden ist, wird sie anschließend 15 Stunden bei 250 bis 3000C in einem Autoklav gehalten. Der ausgefallene Niederschlag, bestehend aus der Viererringverbindung und nebenbei gebildetem Lithiumchlorid, wird abgetrennt und mit Xylol oder Brombenzol extrahiert. Es hinterbleiben 12,1 g Lithiumchlorid, was einem Umsatz von 95 °/0 entspricht.
ίο Der Extrakt besteht aus 19,8 g Hexaphenyl-1,3,2,4-diazadisiletidin (48,5 °/0 der Theorie). Aus Nitrobenzol oder Brombenzol umkristallisiert beträgt der Schmelzpunkt 355,5°C (korrigiert).
Molgewicht
Berechnet
gefunden
546,8,
576.
11,46 g (0,042 Mol) der obigen Verbindung werden in einem mit Rückflußkühler versehenen Kolben zum Sieden erhitzt. Nach kurzer Zeit beginnt die Reaktion und Trimethylsiliciumchlorid destilliert durch den auf 60° C erwärmten Kühler ab. Im Laufe von 3 Stunden steigt die Kolbentemperatur auf 250 bis 270° C, wobei sich der Kolbeninhalt verdickt. Die erkaltete Reaktionsmischung wird mit Hexan versetzt und die Kristalle abgenutscht.
Rohausbeute 6,8 g (80,5 %) l,3-Diphenyl-2,2,4,4-tetramethyl-l,3,2,4-diazadisiletidin; Fp. 252,5°C (aus Xylol umkristallisiert).
Beispiel 2
Aus 14,0 g (0,15 Mol) Anilin und 50 ml Butyllithium (6n-Lösung in Hexan) wird in bekannter Weise das Dilithiumsalz dargestellt.
Zur Suspension des Dilithiumsalzes wird in einer Stickstoffatmosphäre unter Rühren eine Lösung von 95,0 g (0,37 Mol) reines (CeHs)2SiCl2 in 50 ml Xylol
Wenn eine äquimolare Menge Diphenyldichlorsilan verwendet wird, beträgt die Ausbeute an Viererringverbindung nur etwa 23 °/u·

Claims (2)

Patentansprüche:
1. Verfahren zur Herstellung von Cyclodisilazanen nach Patent 1 214 683, dadurch g e kennzeichnet, daß man Disilylamine der allgemeinen Formel
Xp c: TvTl?' QiP V" 3— reiN.«öi — iNiv — οΐχ\.»Λ.3 — η
in der R einen gegebenenfalls halogenierten Alkyl-, Alkenyl-, Cycloalkyl-, Cycloalkenyl-, Aralkyl-, Aralkenyl- oder Arylrest mit bis zu 20 Kohlenstoffatomen oder einen über das Sauerstoffatom gebundenen Rest eines einwertigen Alkohols oder Phenols mit bis zu 20 Kohlenstoffatomen, zwei Reste am gleichen Siliciumatom zusammengenommen einen heterocyclischen Rest, R' einen Alkyl-, Alkenyl-, Cycloalkyl-, Cycloalkenyl-, Aralkyl-, Aralkenyl-, Arylrest oder heterocyclischen Rest mit bis zu 20 Kohlenstoffatomen, X ein Halogenatom und η 0, 1, 2 oder 3 bedeutet und mindestens ein X vorhanden ist, unter Sauerstoffausschluß erhitzt.
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man an Stelle von Disilylaminen Mischungen aus einem Silylamin der Allgemeinen Formel
R'NM — SiR3
in welcher M ein Alkalimetallatom bedeutet, und einem Halogensilan der allgemeinen Formel
SlR 771X4— m
in welcher m 0, 1 oder 2 bedeutet, verwendet.
709 609/465 6.67 © Bundesdruckerei Berlin
DENDAT1252683D 1962-03-30 Verfahren zur Herstellung von Cyclodisilazanen Pending DE1252683B (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH384062A CH407114A (de) 1962-03-30 1962-03-30 Verfahren zur Herstellung heterocyclischer Viererringverbindungen
CH327563A CH460000A (de) 1963-03-15 1963-03-15 Verfahren zur Herstellung von hochtemperaturbeständigen Cyclodisilazanen

Publications (1)

Publication Number Publication Date
DE1252683B true DE1252683B (de) 1967-10-26

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ID=25692633

Family Applications (3)

Application Number Title Priority Date Filing Date
DENDAT1252683D Pending DE1252683B (de) 1962-03-30 Verfahren zur Herstellung von Cyclodisilazanen
DEM56295A Pending DE1214683B (de) 1962-03-30 1963-03-28 Verfahren zur Herstellung von heterocyclischen Viererringverbindungen
DEM74665A Pending DE1291338B (de) 1962-03-30 1964-03-13 Verfahren zur Herstellung von Cyclodisilazanen

Family Applications After (2)

Application Number Title Priority Date Filing Date
DEM56295A Pending DE1214683B (de) 1962-03-30 1963-03-28 Verfahren zur Herstellung von heterocyclischen Viererringverbindungen
DEM74665A Pending DE1291338B (de) 1962-03-30 1964-03-13 Verfahren zur Herstellung von Cyclodisilazanen

Country Status (4)

Country Link
BE (2) BE645148A (de)
DE (3) DE1214683B (de)
GB (2) GB1040726A (de)
NL (1) NL290900A (de)

Also Published As

Publication number Publication date
NL290900A (de)
GB1040726A (en) 1966-09-01
BE645148A (de) 1964-09-14
DE1214683B (de) 1966-04-21
DE1291338B (de) 1969-03-27
BE630249A (de)
GB1063086A (en) 1967-03-30

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