DE721180C - Process for the preparation of fluorinated aliphatic compounds - Google Patents
Process for the preparation of fluorinated aliphatic compoundsInfo
- Publication number
- DE721180C DE721180C DEI48641D DEI0048641D DE721180C DE 721180 C DE721180 C DE 721180C DE I48641 D DEI48641 D DE I48641D DE I0048641 D DEI0048641 D DE I0048641D DE 721180 C DE721180 C DE 721180C
- Authority
- DE
- Germany
- Prior art keywords
- aliphatic compounds
- preparation
- hydrogen fluoride
- fluorinated aliphatic
- acid
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
- C07C53/21—Acids containing three or more carbon atoms containing fluorine
Description
Verfahren zur Herstellung von fluorierten aliphatischen Verbindungen Es wurde gefunden, daß man fluorhaltige aliphatische Verbindungen dadurch herstellen kann, daß man auf Ölsäure, Leinölfettsäure oder Undecylensäure gasförmigen Fluorwasserstoff, zweckmäßigerweise in Gegenwart eines inerten Lösungsmittels, beispielsweise Methylenchlorid oder Tetrachlorkohlenstoff, einwirken läßt. Es ist überraschend, daß es auf diese Weise gelingt, -die erwähnten Verbindungen durch Anlagerung von Fluorwasserstoff an die jeweils vorhandene Doppelbindung in fluorierte Verbindungen überzuführen, ohne daß Polymerisationserscheinungen auftreten, dies um so mehr, als sich in der Literatur gelegentlich die Behauptung findet, Ölsäure werde durch,die Einwirkung von Fluorwasserstoff polymerisiert.Process for the preparation of fluorinated aliphatic compounds It has been found that fluorine-containing aliphatic compounds can be produced in this way can be that on oleic acid, linseed oil fatty acid or undecylenic acid, gaseous hydrogen fluoride, expediently in the presence of an inert solvent, for example methylene chloride or carbon tetrachloride. It is surprising to find it on this Way succeeds in the compounds mentioned by the addition of hydrogen fluoride to convert the double bond present into fluorinated compounds, without polymerization phenomena occurring, all the more so than in the Literature occasionally finds that oleic acid is caused by the action polymerized by hydrogen fluoride.
Beispiele 1. 282 g Ölsäure werden gelöst in etwa Zoo ccm Methylenchlorid oder Tetrachlorkohlezistoff und unter guter Kühlung bei etwa io° mit gasförmigem wasserfreiem Fluorwasserstoff behandelt. Es werden etwa 20 g Fluorwasserstoff aufgenommen. Aus der Reaktionsmasse wird das Lösungsmittel abdestilliert, und es hinterbleibt feste Fluorsbearinsäure. Das aus Alkohol umkristallisierte Produkt besteht aus weißen Blättchen mit einem scharfen Schmelzpunkt von 68°.Examples 1. 282 g of oleic acid are dissolved in about zoo cc of methylene chloride or carbon tetrachloride and with good cooling at about 10 ° with gaseous treated with anhydrous hydrogen fluoride. About 20 g of hydrogen fluoride are absorbed. The solvent is distilled off from the reaction mass and it remains solid fluorobearic acid. The product recrystallized from alcohol consists of white Leaflets with a sharp melting point of 68 °.
2. Man leitet bei 15 bis 2o° in ioo g Ölsäure 3 Stunden lang Fluorwasserstoff ein. Das Reaktionsprodukt kristallisiert aus. Nun wird in Äther gelöst und mit Wasser neutral gewaschen. Ausbeute: ioo g eines schwach gelb gefärbten Körpers, der sich in den gebräuchlichen organischen Lösungsmitteln leicht löst und der, aus Alkohol umkristallisiert, eine Verbindung ligfert, welche mit derjenigen des obigen Beispiels i identisch ist.2. Hydrogen fluoride is passed in 100 g of oleic acid at 15 ° to 20 ° for 3 hours a. The reaction product crystallizes out. Now it is dissolved in ether and with water washed neutral. Yield: 100 g of a pale yellow colored body, which Easily dissolves in common organic solvents and that of alcohol recrystallized, ligfert a compound similar to that of the above example i is identical.
Verwendet man statt der Ölsäure Leinölfettsäure, so erhält man die Anlagerungsverbindung von Fluorwasserstoff an die Doppelbindungen der Leinölfettsäure, ein Produkt von salbenartiger Konsistenz und undefiniertem Schmelzpunkt.If you use linseed oil fatty acid instead of oleic acid, you get the Addition of hydrogen fluoride to the double bonds of linseed oil fatty acid, a product with an ointment-like consistency and an undefined melting point.
3. 188 Gewichtsteile Undecylensäure werden in 3oo Gewichtsteilen Chloroform gelöst. Dann leitet man bei 25 bis 35° gasförmigen Fluorwasserstoff ein bis zur Sättigung. Durch Aufarbeitung, wie in Beispiel i beschrieben, erhält man die Monofluorundecansäure.3. 188 parts by weight of undecylenic acid are dissolved in 300 parts by weight of chloroform solved. Then at 25 to 35 ° gaseous hydrogen fluoride is passed up to Saturation. The monofluorundecanoic acid is obtained by working up as described in Example i.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI48641D DE721180C (en) | 1933-12-23 | 1933-12-23 | Process for the preparation of fluorinated aliphatic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI48641D DE721180C (en) | 1933-12-23 | 1933-12-23 | Process for the preparation of fluorinated aliphatic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE721180C true DE721180C (en) | 1942-05-29 |
Family
ID=7192341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI48641D Expired DE721180C (en) | 1933-12-23 | 1933-12-23 | Process for the preparation of fluorinated aliphatic compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE721180C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0383128A1 (en) * | 1989-02-16 | 1990-08-22 | Bayer Ag | Process for the fluorination of acrylic acid and derivatives thereof, and fluorinated esters of 2,3-difluoropropionic acid |
-
1933
- 1933-12-23 DE DEI48641D patent/DE721180C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0383128A1 (en) * | 1989-02-16 | 1990-08-22 | Bayer Ag | Process for the fluorination of acrylic acid and derivatives thereof, and fluorinated esters of 2,3-difluoropropionic acid |
| US5072030A (en) * | 1989-02-16 | 1991-12-10 | Bayer Aktiengesellschaft | Process for the fluorination of acrylic acid and derivatives thereof and novel fluorinated esters of 2,3-difluoropropionic acid |
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