CH158242A - Process for the production of 1. 6-dibromo-2-oxynaphthalene-3-carboxylic acid. - Google Patents
Process for the production of 1. 6-dibromo-2-oxynaphthalene-3-carboxylic acid.Info
- Publication number
- CH158242A CH158242A CH158242DA CH158242A CH 158242 A CH158242 A CH 158242A CH 158242D A CH158242D A CH 158242DA CH 158242 A CH158242 A CH 158242A
- Authority
- CH
- Switzerland
- Prior art keywords
- bromine
- acid
- carboxylic acid
- oxynaphthalene
- dibromo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von<B>1 .</B> 6-Dibrom-2-oxyna-phtalin-3-earbonsäure. <B>.</B> In der deutschen Patentschrift Nr. 396519 ist ein Verfahren beschrieben zur Herstel lung der<B>1.</B> 6-Dibrom-2-oxynaphtalin-3-ear- bonsäure durch Einwirkung von 4 Atomen Brem auf die 2-Oxynaphtalin-3-earbonsäure, analog dem im Journal fär praktische, Clie- mie.. Band<B>103 (1921/22),</B> Seite<B>369</B> beschrie benen Verfahren.
Das gleiche Resultat wird erhalten gemäss "Berichte der deutschen chemischen Gesell- schafC, Band<B>68 (19,25),</B> Seite<B>2850,</B> durch Einwirkung eines Überschusses von Brom auf j#lonobrom-2-oxynaphtalin-3-earbonsäure. Wendet man Brom in einer Menge ent- spree <B>2</B> Atomen Brom auf<B>1</B> Molekül 'hend <B>9</B> der Naphialinearbonsäure an, so leitet man zweckmässig den entweiehenden Bromwasser stoff in rauchende Schwefelsäure ein und führt das so gebildete Brom mit letzterer als dann wieder der Rea,'ktionsmasse zu.
Da cli(, Schwefelsäure selbst zum Teil Brom aus Bromwasserstoff frei macht, kann man dabei mit weniger als der theoretisch erforderlichen Menge<B>SO,</B> auskommen.
Die so erhaltene Säure ist ein wertvolles Zwisellenpro(lukt zur Herstellung von Farb stoffen. Nach dem Verfahren gemäss vorliegender Erfindung wird die Anwendung derartig hoher Mengen Brom vermieden. Man löst die -9-Oxynaphtalin-3-earbonsäure in Schwe felsäure und fügt der Lösung Brom zu,-und zwar im Verhältnis von 2 bis 2,1 Atomen Brom auf<B>1</B> Molekül der NapUtalinearbon- säure. <I>Beispiel<B>1:
</B></I> <B>75,2</B> Gewichtsteile bonsäure werden in 400 Gewichtsteilen Schwefelsäure 9,5%ig eingetragen, Unter Aussenkü'hlung mit Kältemischung lässt man hierzu bei<B>- 5 ' C 6,5</B> Gewichtsteile Brom langsam innerhalb 2 Stunden zufliessen und lässt dann allmählich die Temperatur auf Zimmertemperatur ansteigen. Nacb_ etwa 20stündigem Stellen wird die Temperatur in<B>6</B> Stunden bis auf<B>50 ' C</B> gebracht und dabei solange gehalten, bis eine in 'Wasser gefällte Probe durch ihren Schmelzpunkt die Beendigung der Reaktion anzeigt.
Die Reah- tionsmasse wird dann in Wasser gegossen, filtriert und der Rückstand mit Wasser neu tral gewaschen und getrocknet.
<I>Beispiel 2:</I> <B>151</B> Gewichtsteile 2-Oxynaphtalin-3-ear- bonsäure werden in<B>650</B> Gewichtsteile Schwe felsäure<B>9,5 %</B> ig eingetragen. Unter Aussenküh lung mit Kältemischung lässt man hierzu bei <B>- -5 ' C</B> bis<B>0 ' C 129-</B> Gewichtsteile Brom langsam zufliessen, wobei man etwa ent weichenden Bromwasserstoff in<B>320</B> Gewichts teile rauchender Schwefelsäure 20 /lo ig ein leitet, die man alsdann der Reaktionsmasse langsam wieder zuleitet. Man rührt bei Zimmertemperatur noch einige Stunden bis zur Vollendung der Reaktion.
Die Reak tionsmasse wird alsdann in 2000, Gewichts teile Eiswasser gegossen, abfiltriert und mit Wasser neutral gewaschen und getrocknet.
Process for the preparation of <B> 1. </B> 6-dibromo-2-oxyna-phthalene-3-carboxylic acid. <B>. </B> The German patent specification No. 396519 describes a process for the production of <B> 1. </B> 6-dibromo-2-oxynaphthalene-3-earboxylic acid by the action of 4 atoms Brem on the 2-oxynaphthalene-3-carboxylic acid, analogous to the method described in the journal fär practical, Clie- mie .. Volume 103 (1921/22), page 369 .
The same result is obtained according to "Reports of the German Chemical Society, Volume <B> 68 (19.25), </B> Page <B> 2850, </B> by the action of an excess of bromine on j # lonobromium -2-oxynaphthalene-3-carboxylic acid. If you use bromine in an amount equivalent to <B> 2 </B> atoms of bromine on <B> 1 </B> molecule <B> 9 </B> of the naphialinearboxylic acid on, the escaping hydrogen bromine is expediently introduced into fuming sulfuric acid and the bromine thus formed is then returned to the reaction mass with the latter.
Since cli (, sulfuric acid itself partially liberates bromine from hydrogen bromide, less than the theoretically required amount of <B> SO, </B> can be used.
The acid thus obtained is a valuable intermediate product for the production of dyes. The process according to the present invention avoids the use of such high amounts of bromine. The -9-oxynaphthalene-3-carboxylic acid is dissolved in sulfuric acid and bromine is added to the solution to, in a ratio of 2 to 2.1 atoms of bromine to <B> 1 </B> molecule of naputalinearic acid. <I> Example <B> 1:
</B> </I> <B> 75.2 </B> parts by weight of boric acid are added to 400 parts by weight of 9.5% sulfuric acid, while external cooling with a cold mixture, it is left at <B> -5 'C 6 , 5 parts by weight of bromine slowly flow in over 2 hours and then gradually allow the temperature to rise to room temperature. After about 20 hours of exposure, the temperature is brought to <B> 50 ° C </B> in <B> 6 </B> hours and held there until a sample precipitated in water indicates the end of the reaction by its melting point .
The reaction mass is then poured into water, filtered and the residue washed neutral with water and dried.
<I> Example 2: </I> <B> 151 </B> parts by weight of 2-oxynaphthalene-3-earboxylic acid are converted into <B> 650 </B> parts by weight of sulfuric acid <B> 9.5% </ B> ig registered. For this purpose, with external cooling with a cold mixture, at <B> - -5 'C </B> to <B> 0' C 129- </B> parts by weight of bromine are allowed to slowly flow in, with any escaping hydrogen bromide in <B> 320 </B> Part by weight of fuming sulfuric acid 20 / lo ig introduces, which is then slowly fed back into the reaction mass. The mixture is stirred for a few hours at room temperature until the reaction has ended.
The reaction mass is then poured into 2000 parts by weight of ice water, filtered off, washed neutral with water and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE158242X | 1931-01-06 | ||
| DE50531X | 1931-05-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH158242A true CH158242A (en) | 1932-11-15 |
Family
ID=25749142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH158242D CH158242A (en) | 1931-01-06 | 1931-12-18 | Process for the production of 1. 6-dibromo-2-oxynaphthalene-3-carboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH158242A (en) |
-
1931
- 1931-12-18 CH CH158242D patent/CH158242A/en unknown
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