CH202419A - Process for producing an organic bromine compound. - Google Patents
Process for producing an organic bromine compound.Info
- Publication number
- CH202419A CH202419A CH202419DA CH202419A CH 202419 A CH202419 A CH 202419A CH 202419D A CH202419D A CH 202419DA CH 202419 A CH202419 A CH 202419A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- bromine compound
- organic bromine
- producing
- hexadecanedioic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 150000005526 organic bromine compounds Chemical class 0.000 title claims description 4
- 150000003839 salts Chemical class 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 3
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 3
- OLACPKKVZSLCSI-UHFFFAOYSA-N 15-bromopentadecanoic acid Chemical compound OC(=O)CCCCCCCCCCCCCCBr OLACPKKVZSLCSI-UHFFFAOYSA-N 0.000 claims description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- QQHJDPROMQRDLA-UHFFFAOYSA-N hexadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCC(O)=O QQHJDPROMQRDLA-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- -1 monocarboxylic acid ester Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer organischen Brom-verbindung. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung einer organischen Bromverbindung, das dadurch gekennzeich net ist, dass man auf ein Metallsalz eines Hexadecandisäure-1 . 16-monoesters elemen tares Brom einwirken lässt und den entstan denen 15-Brompentadecansäure-l-ester mit einem verseifenden Mittel in die freie bro- mierte Monocarbonsäure überführt.
Die so erhaltene 15-Brompentadecan- säure-1 ist in der Literatur bereits beschrie ben. Sie soll als Zwischenprodukt bei der Herstellung von Riechstoffen und Arznei mitteln dienen.
Als besonders geeignet erwiesen sich das Silbersalz, die Mercuro- und Mercurisalze, sowie das Thallosalz der halbseitig verester- ten Dicarbonsäure.
Vorteilhaft arbeitet man in Gegenwart. von indifferenten Lösungs- oder Verdün nungsmitteln, wie Luft, CC14, CHCl" oder Äther.
Zur Verseifung des bromierten Monocar- bonsäureesters verwendet man mit Vorteil eine Eisessig-Bromwasserstofflösung.
<I>Beispiel:</I> Zu einer Aufschlämmung von 421 g Sil bersalz des Hexadecandisäure-monoesters in 800 g Tetrachlorkohlenstoff gibt man unter Vermeidung zu starker Erwärmung nach und nach 50 bis 55 cm' trockenes Brom, und zwar so lange, bis kein Brom mehr ver braucht wird.
Die Lösung wird vom AgBr abfiltriert, das AgBr am @Soxhlet mit Tetra- chlorkohlenstoff extrahiert und die vereinig ten Filtrate destilliert.
Nach dem Entfernen des Tetrachlorkohlenstoffes wird der Rüok- stand mit Eisessig aufgenommen, abgekühlt und nach dem Filtrieren eines geringen Nie derschlages unter Zusatz von etwas Hssr ver seift.
Nach der Verseifung wird die Lösung mit Aktivkohle entfärbt und abgekühlt. Hier- bei. kristal,lisieren12'34,g 15-Brompentadecandi- säure vom F = 63-65 -aus; das sind <B>73A</B> der Theorie.
Process for the preparation of an organic bromine compound. The subject of the present patent is a process for the preparation of an organic bromine compound, which is characterized in that a metal salt of a hexadecanedioic acid-1. 16-monoester elementary bromine can act and the resulting 15-bromopentadecanoic acid l-ester is converted into the free brominated monocarboxylic acid with a saponifying agent.
The 15-bromopentadecanoic acid-1 obtained in this way has already been described in the literature. It should serve as an intermediate product in the manufacture of fragrances and drugs.
The silver salt, the mercurous and mercuric salts, and the thallo salt of the half-esterified dicarboxylic acid have proven to be particularly suitable.
It is advantageous to work in the present. of indifferent solvents or diluents such as air, CC14, CHCl "or ether.
A glacial acetic acid / hydrogen bromide solution is advantageously used to saponify the brominated monocarboxylic acid ester.
<I> Example: </I> To a slurry of 421 g of the silver salt of the hexadecanedioic acid monoester in 800 g of carbon tetrachloride, 50 to 55 cm 'of dry bromine are gradually added, while avoiding excessive heating, until no Bromine is consumed more.
The solution is filtered off from the AgBr, the AgBr is extracted on the @Soxhlet with carbon tetrachloride and the combined filtrates are distilled.
After the carbon tetrachloride has been removed, the residue is taken up with glacial acetic acid, cooled and, after filtering, a slight precipitate is soaped off with the addition of a little Hssr.
After the saponification, the solution is decolorized with activated charcoal and cooled. Here. crystalline, lize12'34, g of 15-bromopentadecanedic acid from F = 63-65; these are <B> 73A </B> of theory.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH202419T | 1937-08-20 | ||
| CH199454T | 1938-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH202419A true CH202419A (en) | 1939-01-15 |
Family
ID=25723281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH202419D CH202419A (en) | 1937-08-20 | 1937-08-20 | Process for producing an organic bromine compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH202419A (en) |
-
1937
- 1937-08-20 CH CH202419D patent/CH202419A/en unknown
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