CH174643A - Process for the isolation of dibenzoxanthones from a residue of 2,3-oxynaphthoic acid production. - Google Patents
Process for the isolation of dibenzoxanthones from a residue of 2,3-oxynaphthoic acid production.Info
- Publication number
- CH174643A CH174643A CH174643DA CH174643A CH 174643 A CH174643 A CH 174643A CH 174643D A CH174643D A CH 174643DA CH 174643 A CH174643 A CH 174643A
- Authority
- CH
- Switzerland
- Prior art keywords
- dibenzoxanthones
- residue
- isolation
- oxynaphthoic acid
- acid production
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- OCISOSJGBCQHHN-UHFFFAOYSA-N 3-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(O)=CC2=C1 OCISOSJGBCQHHN-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002955 isolation Methods 0.000 title claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Verfahren zur Isolierung von Dibenzoxanthonen ans einem Rückstand der 2.3-Oxynaphthoesänrefabrikation. Bei der Fabrikation der 2.3-Oxynaph- thoesäure ei-hält man neben unverändertem 13-Naphthol gewisse Mengen eines in Alkalien unlöslichen Harzes.
Es wurde gefunden, dass man aus diesem Harze bei einer Behandlung mit LösuDgsmit- teln der Pyridinreihe, vorzugsweise technisches Pyridin, zwei Dibenzoxanthone isolieren kann, von welchen das eine vom S. P 194,5 o bis <B>195,50</B> mit dem bereits bekannten Dibenz- oxanthon der Formel
EMI0001.0014
übereinstimmt, während dem andern, bis an- hin unbekannten Dibenzoxanthon vom S. P. 184 o bis 185,5' wahrscheinlich die Formel
EMI0001.0019
zukommt.
Beide Dibenzoxanthone sollen zur Herstellung von Zwischenprodukten, sowie von Farbstoffen verwendet werden.
<I>Beispiel 1:</I> 100 Teile des laugenunlöslichen Rückstan des, der bei der Herstellung der 2. 3 - Oxy- naphthoesäure nach dem Verfahren des D. R. P. Nr. 423034 entsteht, werden mit 200 Teilen 90 o%oigem Pyridin kurze Zeit rückfliessend im Sieden erhalten und die Lö sung siedend heiss filtriert. Beim Erkalten kristallisiert das Gemisch der Dibenzoxan- thone aus; durch Absaugen, Auswaschen zu- erst mit kaltem, dann mit siedendem Wasser, wird es vom Pyridin befreit und getrocknet.
Zur Trennung des Gemisches der Dibenz- oxantlione kann folgendermassen verfahren werden: 100 Teile des erhaltenen Gemisches wer- den mit 700 Teilen 80 %igem Pyridin zum Sieden erhitzt und siedend heiss filtriert.
Als Rückstand verbleiben, nach Befreiung vom Pyridin durch Auswaschen mit siedendem Wasser und Trocknen, 29 Teile Dibenzoxan- thon, welches nach Kristallisation aus Toluol den S. P. 190-1920 aufweist. Es löst sich in konzentrierter Schwefelsäure grüngelb mit grüner Fluoreszenz. Durch weiteres Kristal lisieren kann der Siedepunkt auf 195 0 ge bracht werden.
Aus dem Filtrat kristallisieren 59 Teile Dibenzoxanthon aus, die, wie oben ange geben, vom Pyridin befreit werden. Nach der Kristallisation aus Toluol schmilzt es bei 179-181'. Durch weiteres Kristallisieren kann der S. P. auf 1840 gebracht werden. In Schwefelsäure löst es sich braungelb mit schwach grüner Fluoreszenz. <I>Beispiel 2:</I> Etwas kürzer gestaltet sich das Verfah ren, wenn die Trennung schon direkt am Harz vorgenommen wird.
In diesem Falle wird 1 Teil Harz mit 2-3,25 Teilen 80 %- igem Pyridin zum Sieden erhitzt, wobei im Rückstand Dibenzoxanthon vom S. P. 190 bis<B>1921</B> verbleibt, während im Filtrat Di- benzoxanthon mit dem S P. 179-1810 aus kristallisiert. Zum Reinigen werden beide Produkte aus Toluol umkristallisiert.
Process for the isolation of dibenzoxanthones from a residue from 2,3-Oxynaphthoesänrefabrikation. In the manufacture of 2,3-oxynaphthoic acid, in addition to unchanged 13-naphthol, certain quantities of a resin which is insoluble in alkalis are kept.
It has been found that, when treated with solvents of the pyridine series, preferably technical grade pyridine, two dibenzoxanthones can be isolated from these resins, one of which is described in pp. 194.5 to 195.50 > with the already known dibenzoxanthone of the formula
EMI0001.0014
agrees, while the other, hitherto unknown dibenzoxanthone from pp. 184o to 185.5 'probably has the formula
EMI0001.0019
comes to.
Both dibenzoxanthones are to be used for the production of intermediate products and dyes.
<I> Example 1: </I> 100 parts of the alkali-insoluble residue, which arises in the production of the 2,3-oxynaphthoic acid according to the method of DRP No. 423034, are mixed with 200 parts of 90% pyridine for a short time Keep refluxing at the boil and the solution filtered boiling hot. When cooling down, the mixture of dibenzoxanthones crystallizes out; it is freed from pyridine and dried by suction, washing out first with cold and then with boiling water.
The following procedure can be used to separate the mixture of dibenzoxantliones: 100 parts of the mixture obtained are heated to boiling with 700 parts of 80% strength pyridine and filtered while boiling.
After the pyridine has been removed by washing with boiling water and drying, the residue remains 29 parts of dibenzoxanthone, which, after crystallization from toluene, has pp. 190-1920. It dissolves in concentrated sulfuric acid green-yellow with green fluorescence. The boiling point can be brought to 195 0 by further crystallization.
59 parts of dibenzoxanthone crystallize out from the filtrate and, as stated above, are freed from pyridine. After crystallization from toluene, it melts at 179-181 '. The S.P. can be brought to 1840 by further crystallization. In sulfuric acid, it dissolves brownish-yellow with weak green fluorescence. <I> Example 2: </I> The process is somewhat shorter if the separation is already carried out directly on the resin.
In this case, 1 part of resin is heated to boiling with 2-3.25 parts of 80% pyridine, with dibenzoxanthone from SP 190 to 1921 remaining in the residue, while dibenzoxanthone with the S in the filtrate P. 179-1810 crystallized from. For cleaning, both products are recrystallized from toluene.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH174643T | 1933-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH174643A true CH174643A (en) | 1935-01-31 |
Family
ID=4425610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH174643D CH174643A (en) | 1933-12-23 | 1933-12-23 | Process for the isolation of dibenzoxanthones from a residue of 2,3-oxynaphthoic acid production. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH174643A (en) |
-
1933
- 1933-12-23 CH CH174643D patent/CH174643A/en unknown
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