DE739579C - Process for the preparation of compounds of boron fluoride - Google Patents
Process for the preparation of compounds of boron fluorideInfo
- Publication number
- DE739579C DE739579C DEI65789D DEI0065789D DE739579C DE 739579 C DE739579 C DE 739579C DE I65789 D DEI65789 D DE I65789D DE I0065789 D DEI0065789 D DE I0065789D DE 739579 C DE739579 C DE 739579C
- Authority
- DE
- Germany
- Prior art keywords
- boron fluoride
- compounds
- weight
- parts
- preparation
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/10—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring unsubstituted
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
Description
Verfahren zur Herstellung von Verbindungen des Borfluorids Es wurde gefunden, daß man zu kristallisierten Verbindungen des Borfluorids mit Laktonen von der Formel gelangt, wenn man Laktone mit Borfluorid -zusammenbringt.Process for the preparation of compounds of boron fluoride It has been found that crystallized compounds of boron fluoride with lactones of the formula when lactones are combined with boron fluoride.
Die Reaktion verläuft am besten bei Temperaturen um 3o bis 5o°, doch bilden sich die Verbindungen auch bei höheren und niedrigeren Temperaturen. Die Verbindungen sind zum Teil unzersetzt im Hochvakuum destillierbar. So siedet die Borfluoridverbindung des Butyrolaktons unter o,o5 mm Druck bei 75°. Es können auch Verbindungen des Borfluorids, z. B. das Borfluoridhydrat, angewandt werden.The reaction works best at temperatures around 3o to 5o °, but the connections also form at higher and lower temperatures. the Some of the compounds can be distilled in a high vacuum without decomposing. So it boils Boron fluoride compound of butyrolactone under 0.05 mm pressure at 75 °. It can too Compounds of boron fluoride, e.g. B. the boron fluoride hydrate can be used.
Die neuen wohldefinierten Verbindungen des Borfluorids können als Katalysatoren, insbesondere bei Umsetzungen, die unter Mitverwendung von Laktonen ausgeführt werden, mit Vorteil Verwendung finden. Sie eignen sich ausgezeichnet als Katalysatoren für Friedel-Craftssche Umsetzungen.The new well-defined compounds of boron fluoride can be used as Catalysts, especially in reactions involving the use of lactones are carried out, are used with advantage. They are excellent as catalysts for Friedel-Crafts reactions.
Beispiel r Man leitet in Butyrolakton Borfluorid ein; die Temperatur steigert sich auf etwa d0°, und nach einiger Zeit erstarrt die Masse zu einem Brei. Man saugt dann von dem nicht umgesetzten Butyrolakton ab und erhält die feste Verbindung in einer Ausbeute von etwa 8o°(0. Sie ist in überschüssigem Butyrolakton löslich, unlöslich in Benzin und Chlorkohlenwasserstoffen. Ihr Erstarrungspunkt liegt bei etwa 6o bis 62°.Example r Boron fluoride is introduced into butyrolactone; the temperature increases to about d0 °, and after a while the mass solidifies to a pulp. The unreacted butyrolactone is then suctioned off and the solid compound is obtained in a yield of about 80 ° (0. It is in excess butyrolactone soluble, insoluble in gasoline and chlorinated hydrocarbons. Your freezing point is around 6o to 62 °.
Beispiel e Man leitet Borfluorid in 22o Gewichtsteile y-Valerolakton bis zur Sättigung ein. Die Temperatur steigt allmählich auf 6o bis 65°, und es werden etwa 154 Gewichtsteile Borfluorid aufgenommen. Das erhaltene dickflüssige Öl siedet unter 2o mm HB-Druck bei I io bis i I 11, wobei nur geringe Wengen Borfluorid abgespalten werden. Die Ausbeute beträgt etwa 9o °/o der Theorie.Example e Boron fluoride is introduced into 220 parts by weight of y-valerolactone until saturation is achieved. The temperature rises gradually to 60 to 65 °, and about 154 parts by weight of boron fluoride are taken up. The viscous oil obtained boils under 20 mm HB pressure at 10 to 10 11, with only a small amount of boron fluoride being split off. The yield is about 90% of theory.
Beispiel 3 114 Gewichtsteile 4-Undekalakton werden bei - 6o bis 70° mit Borfluorid , gesättigt. Die Aufnahme an Borfluorid beträgt etwa 4o Gewichtsteile. Man erhält ein zähflüssiges 01. Es ist in einem Vakuum von etwa 2o mm HB-Druck nicht unzersetzt destillierbar.Example 3 114 parts by weight of 4-undecalactone are saturated with boron fluoride at -6o to 70 °. The uptake of boron fluoride is about 40 parts by weight. A viscous oil is obtained. It cannot be distilled without decomposition in a vacuum of about 20 mm HB pressure.
Beispiel 4 5o Gewichtsteile Hexahydrophthalid «-erden bei 6o bis 70° mit Borfluorid gesättigt, wobei ein bei 62° schmelzendes, kristallisiertes Produkt entsteht, das auf i Mol Lakton i Mol Borfluorid enthält. Es ist in einem Vakuum von i mm Quecksilberdruck nicht unzersetzt destillierbar.Example 4 50 parts by weight of hexahydrophthalide «-Erden saturated at 6o to 70 ° with boron fluoride, a crystallized product melting at 62 ° is formed which contains 1 mole of lactone and 1 mole of boron fluoride. It cannot be distilled without decomposition in a vacuum of 1 mm mercury pressure.
Beispiel 5 Man löst 5o Gewichtsteile Cumarin in ioo Gewichtsteilen Methylenchlorid und sättigt die Lösung bei 40° mit Borfluorid. Es scheiden sich bald weiße hygroskopische Kristalle aus. Ein großer Teil des Umsetzungsproduktes bleibt in Lösung und kann daraus durch Verdunsten des Lösungsmittels gewonnen werden. Das Umsetzungsprodukt schmilzt unter teilweiser Zersetzung bei 152°. Beispiel 6 Man leitet in eine Lösung von 49 Gewichtsteilen Phthalid in Zoo Gewichtsteilen Tetrachlorkohlenstoff bei 6o° Borfluorid ein, bis die Gewichtszunahme 32 Gewichtsteile beträgt. Man erhält 49 Gewichtsteile eines weißen kristallinen Körpers. Beim Verdampfen des Tetrachlorkohlenstoffs erhält man weitere 25 Gewichtsteile der Anlagerungsverbindung. Sie schmilzt bei etwa 8o bis 84° unter Zersetzung und ist nicht unzersetzt destillierbar.EXAMPLE 5 50 parts by weight of coumarin are dissolved in 100 parts by weight of methylene chloride and the solution is saturated at 40 ° with boron fluoride. White, hygroscopic crystals soon separate. A large part of the reaction product remains in solution and can be obtained therefrom by evaporation of the solvent. The reaction product melts with partial decomposition at 152 °. Example 6 A solution of 49 parts by weight of phthalide is passed through in zoo parts by weight of carbon tetrachloride at 60 ° boron fluoride until the weight gain is 32 parts by weight. 49 parts by weight of a white crystalline body are obtained. When the carbon tetrachloride evaporates, another 25 parts by weight of the addition compound are obtained. It melts at about 80 to 84 ° with decomposition and cannot be distilled without decomposition.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI65789D DE739579C (en) | 1939-10-13 | 1939-10-13 | Process for the preparation of compounds of boron fluoride |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI65789D DE739579C (en) | 1939-10-13 | 1939-10-13 | Process for the preparation of compounds of boron fluoride |
Publications (1)
Publication Number | Publication Date |
---|---|
DE739579C true DE739579C (en) | 1943-09-29 |
Family
ID=7196404
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEI65789D Expired DE739579C (en) | 1939-10-13 | 1939-10-13 | Process for the preparation of compounds of boron fluoride |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE739579C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008149612A1 (en) | 2007-05-29 | 2008-12-11 | Toyota Jidosha Kabushiki Kaisha | Asymmetric bf3 complex |
-
1939
- 1939-10-13 DE DEI65789D patent/DE739579C/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008149612A1 (en) | 2007-05-29 | 2008-12-11 | Toyota Jidosha Kabushiki Kaisha | Asymmetric bf3 complex |
EP2163537A1 (en) * | 2007-05-29 | 2010-03-17 | Toyota Jidosha Kabushiki Kaisha | Asymmetric bf3 complex |
EP2163537A4 (en) * | 2007-05-29 | 2011-08-03 | Toyota Motor Co Ltd | Asymmetric bf3 complex |
US8765294B2 (en) | 2007-05-29 | 2014-07-01 | Toyota Jidosha Kabushiki Kaisha | Asymmetric type BF3 complex |
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