DE1115249B - Process for the preparation of alkoxy-, aroxy- or alkylalkoxy-boralkylenes - Google Patents
Process for the preparation of alkoxy-, aroxy- or alkylalkoxy-boralkylenesInfo
- Publication number
- DE1115249B DE1115249B DEK33271A DEK0033271A DE1115249B DE 1115249 B DE1115249 B DE 1115249B DE K33271 A DEK33271 A DE K33271A DE K0033271 A DEK0033271 A DE K0033271A DE 1115249 B DE1115249 B DE 1115249B
- Authority
- DE
- Germany
- Prior art keywords
- aroxy
- alkoxy
- alkylalkoxy
- preparation
- boralkylenes
- 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
- 125000003545 alkoxy group Chemical group 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001336 alkenes Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910000095 alkaline earth hydride Inorganic materials 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 238000007323 disproportionation reaction Methods 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- -1 boric acid ester Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- KUGSJJNCCNSRMM-UHFFFAOYSA-N ethoxyboronic acid Chemical compound CCOB(O)O KUGSJJNCCNSRMM-UHFFFAOYSA-N 0.000 description 1
- BQXWYPNPICLINV-UHFFFAOYSA-N ethyl dimethyl borate Chemical compound CCOB(OC)OC BQXWYPNPICLINV-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000126 substance 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
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
Verfahren zur Herstellung von Alkoxy-, Aroxy-oder Alkylalkoxy-boralkylen Das Patent 1 044 055 betrifft ein Verfahren zur Herstellung von Alkoxy-, Aroxy- oder Alkylalkoxyborinen, das dadurch gekennzeichnet ist, daß mittels Alkali- oder Erdalkalihydriden oder deren Gemischen Alkoxy-, Aroxy- oder Alkylhalogenborsäureester hydriert werden, wobei das Alkali- oder Erdalkalihydrid durch einen geringen Zusatz von Borsäureester vor der Reaktion aktiviert werden kann. Process for the preparation of alkoxy-, aroxy- or alkylalkoxy-boralkylenes The patent 1 044 055 relates to a process for the preparation of alkoxy, aroxy or alkylalkoxyborines, which is characterized in that by means of alkali or Alkaline earth hydrides or mixtures thereof, alkoxy, aroxy or alkylhaloboric acid esters are hydrogenated, the alkali or alkaline earth hydride by a small addition can be activated by boric acid ester before the reaction.
Es wurde nun gefunden, daß sich an die vorgenannten Borine günstig Olefine anlagern lassen, wobei aus den Borwasserstoffverbindungen die entsprechenden Boralkylverbindungen hergestellt werden. Beispielsweise wird Äthylen an ein Dialkoxyborin angelagert nach der Gleichung R bedeutet darin eine Alkyl- oder Arylgruppe. Die Reaktion wird vorzugsweise unter Druck und bei erhöhter Temperatur durchgeführt. Die Olefinanlagerung läuft als nachgeschaltete Verfahrensstufe je nach den Erfordernissen in An- oder Abwesenheit eines Lösungsmittels ab.It has now been found that olefins can advantageously be added to the abovementioned borines, the corresponding boron alkyl compounds being prepared from the boron hydrogen compounds. For example, ethylene is attached to a dialkoxyborine according to the equation R therein denotes an alkyl or aryl group. The reaction is preferably carried out under pressure and at an elevated temperature. The addition of olefins takes place as a downstream process stage in the presence or absence of a solvent, depending on the requirements.
Aus dem Journal of the American Chemical Society, 55 (1933), S. 4020 ff., ist bekannt, daß die Disproportionierung von Dimethoxyborin sehr langsam vor sich geht, während Hurd, »An Introduction to the Chemistry of the Hydrides«, New York 1952, S. 91, schildert, daß Dimethoxyborin bei Zimmertemperatur schnell disproportioniert. Eigene Beobachtungen bestätigen die Angaben von Hurd, woraus zu schließen wäre, daß die derartig instabilen Alkoxyborine für die Reaktion mit Olefinen nicht geeignet seien. Da ferner bekannt ist, daß Diboran, welches bei der Disproportionierung frei gemacht wird, sehr leicht mit Olefinen unter Bildung von Bortrialkylen reagiert, hätten nach der Disproportionierung von Dimethoxyborin und der Reaktion mit Olefinen Bortrialkyle neben Borsäureestern vorliegen müssen. Daß das nicht der Fall ist, sondern dabei alkylierte Borsäureester entstehen, war daher bei dem erfindungsgemäßen Verfahren nicht ohne weiteres zu erwarten. From the Journal of the American Chemical Society, 55 (1933), p. 4020 ff., it is known that the disproportionation of dimethoxyborine occurs very slowly while Hurd, "An Introduction to the Chemistry of the Hydrides," New York 1952, p. 91, states that dimethoxyborine disproportionates rapidly at room temperature. Our own observations confirm the information provided by Hurd, from which we can conclude that that such unstable alkoxyborines are not suitable for the reaction with olefins be. Since it is also known that diborane, which in the disproportionation free reacts very easily with olefins to form boron trialkyls, would have after disproportionation of dimethoxyborine and reaction with olefins Boron trialkyls must be present in addition to boric acid esters. That this is not the case rather, alkylated boric acid esters are formed in the process, was therefore in the case of the invention Proceedings are not to be expected without further ado.
Die erhaltenen alkylierten Borsäureester lassen sich insbesondere als Katalysatoren, unter anderem für Polymerisationen, gut verwenden. The alkylated boric acid esters obtained can be in particular use well as catalysts, including for polymerizations.
Beispiel 28 Gewichtsteile eines Gemisches von Borsäuretrimethylester und Dimethoxyborin bei einem 250/0eigen Anteil an Dimethoxyborin wurden in ein l-l-Druckgefäß gefüllt. Unter Aufpressung von 20 atü Äthylen wurde das Reaktionsgefäß allmählich auf 160"C erwärmt. Nach Istündiger Reaktionsdauer und anschließendem Abkühlen wurde das iiberschüssige Äthylen abgelassen. Es wurden 30 Gewichtsteile eines Gemisches von Borsäuretrimethylester und Äthylborsäuredimethylester erhalten. Während 1 g des Ausgangsgemisches bei der Hydrolyse 85 ccm Wasserstoff lieferte, entwickelte sich bei der Hydrolyse des Endproduktes kein Wasserstoff mehr; das eingesetzte Dimethoxyborin war demnach quantitativ mit Äthylen in Äthylborsäuredimethylester übergeführt worden. Example 28 parts by weight of a mixture of trimethyl borate and dimethoxyborine at 250/0 Portion of dimethoxyborine were placed in a 1-liter pressure vessel filled. With the injection of 20 atmospheres of ethylene, the reaction vessel gradually became heated to 160 ° C. After a reaction time of 1 hour and subsequent cooling, was the excess ethylene drained. There were 30 parts by weight of a mixture obtained from trimethyl borate and dimethyl ethyl borate. While 1 g of the starting mixture provided 85 cc of hydrogen during hydrolysis During the hydrolysis of the end product, there is no longer any hydrogen; the dimethoxyborine used was therefore quantitatively converted with ethylene into ethyl boric acid dimethyl ester.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK33271A DE1115249B (en) | 1956-12-12 | 1956-12-12 | Process for the preparation of alkoxy-, aroxy- or alkylalkoxy-boralkylenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK33271A DE1115249B (en) | 1956-12-12 | 1956-12-12 | Process for the preparation of alkoxy-, aroxy- or alkylalkoxy-boralkylenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1115249B true DE1115249B (en) | 1961-10-19 |
Family
ID=7219679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK33271A Pending DE1115249B (en) | 1956-12-12 | 1956-12-12 | Process for the preparation of alkoxy-, aroxy- or alkylalkoxy-boralkylenes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1115249B (en) |
-
1956
- 1956-12-12 DE DEK33271A patent/DE1115249B/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
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