CH204855A - Process for the preparation of 1, 4, 5, 8 tetraminoanthraquinone. - Google Patents
Process for the preparation of 1, 4, 5, 8 tetraminoanthraquinone.Info
- Publication number
- CH204855A CH204855A CH204855DA CH204855A CH 204855 A CH204855 A CH 204855A CH 204855D A CH204855D A CH 204855DA CH 204855 A CH204855 A CH 204855A
- Authority
- CH
- Switzerland
- Prior art keywords
- heated
- tetraminoanthraquinone
- tetrachloranthraquinone
- mixture
- ammonium acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- JSFUMBWFPQSADC-UHFFFAOYSA-N Disperse Blue 1 Chemical compound O=C1C2=C(N)C=CC(N)=C2C(=O)C2=C1C(N)=CC=C2N JSFUMBWFPQSADC-UHFFFAOYSA-N 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- DUJPMUKIEFLXRE-UHFFFAOYSA-N 1,4,5,8-tetrachloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C(Cl)=CC=C2Cl DUJPMUKIEFLXRE-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- -1 carboxylic acid imides Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/22—Dyes with unsubstituted amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé de préparation de la 1, 4, 5, 8 tétraminoanthraquinone. La préparation de la 1, 4, 5, 8 tétrami- noanthraquinone peut se faire en traitant la 1, 4, 5, 8 tétrachloroanthraquinone à l'aide des imides d'acides carboxyliques, comme par exemple la phtalimide.
L'utilisation de ce procédé oblige à créer, à côté de la fabrication principale, une petite fabrication secondaire, ce qui est une augmen tation du prix de revient et une augmentation du matériel utilisé.
La demanderesse a trouvé qu'il n'était pas nécessaire de former séparément l'imide et qu'il était plus simple d'employer du phta- late acide d'ammonium.
La présente invention a donc pour objet un procédé de préparation de la 1, 4, 5, 8 tétraminoanthraquinone, caractérisé en ce que l'on chauffe un mélange de 1, 4, 5, 8 tétra- chloranthraquinone et de phtalate acide d'am monium, de façon à former de la tétraphtal- imidoanthraquinone, qui est ensuite hydrolysée.
La réaction de formation de la tétraphtal- imidoanthraquinone est conduite de préférence dans un milieu à base d'anhydride phtalique. Selon une forme très simple d'exécution du procédé, on ajoute une faible quantité d'ammoniaque à de l'anhydride phtalique et l'on ajoute ensuite de la 1, 4, 5, 8 tétrachlor- anthraquinone. Ces additions se font sur l'an hydride phtalique, que l'on emploie en grand excès et qui sert de milieu ,réactionnel.
Les quantités d'eau ainsi introduites sont éliminées par chauffage à 150-180'; à ce moment, on ajoute les autres réactifs et la condensation s'effectue pour aboutir finalement à la tétra- phtalimidoanthraquinone. Ce dernier produit est traité comme â l'ordinaire par un agent hydrolysant pour donner la tétraminoanthra- quinone.
Voici deux exemples d'exécution du pro cédé de l'invention Exemple <I>1:</I> Dans un récipient réactionnel, on introduit d'abord 309 g d'anhydride phtalique et 80 g d'une solution d'ammoniaque à 16% et on chauffe à 150-1800 jusqu'à élimination des vapeurs d'eau, ce qui peut durer environ de 2 à 3 heures. On ajoute 'ensuite dans la masse fondue ainsi obtenue un mélange constitué par: 50 g tétrachloranthraquinone, 50 g carbonate de potassium, et 0,5 g de cuivre en poudre.
A ce moment, la température est amenée à 225-230 C. Au bout de 18 heures de chauffage, la condensation est pratiquement terminée. On extrait l'excès d'anhydride phta lique à l'eau bouillante et la tétraphtalimido- anthraquinonerésultante estsaponifiée à l'aide de 400 g d'acide sulfurique à 66", d'abord à 40 C pendant 12 heures et, finalement, à <B>900</B> pendant 1 heure. La masse réactionnelle est précipitée dans 15 1 d'eau, le sulfate de tétraminoanthraquinone est lavé, puis on li bère la base sur le filtre même à l'aide d'une solution diluée de carbonate de soude.
Natu rellement, le produit final peut être séché tel quel, ou mélangé avant séchage avec des produits destinés à faciliter sa dispersion ul térieure dans les bains de teinture. Exesyaple <I>2:</I> On introduit dans une cuve à réaction 131 g de phtalate acide d'ammonium et 200 g d'anhydride phtalique qu'on amène à fusion par chauffage à 150-1800.
On ajoute ensuite dans la masse fondue ainsi obtenue un mélange constitué par: 50 g tétrachloranthraquinone, 50 g carbonate de potassium, 0,5 g de cuivre en poudre.
On chauffe le tout à 225-230 C pendant 18 heures environ. La suite du traitement s'effectue comme dans l'exemple 1.
Process for the preparation of 1, 4, 5, 8 tetraminoanthraquinone. The preparation of 1, 4, 5, 8 tetraminoanthraquinone can be carried out by treating 1, 4, 5, 8 tetrachloroanthraquinone with the aid of carboxylic acid imides, such as, for example, phthalimide.
The use of this process makes it necessary to create, besides the main production, a small secondary production, which is an increase in the cost price and an increase in the material used.
We have found that it is not necessary to form the imide separately and that it is simpler to use ammonium acid phthalate.
The present invention therefore relates to a process for the preparation of 1, 4, 5, 8 tetraminoanthraquinone, characterized in that a mixture of 1, 4, 5, 8 tetrachloranthraquinone and acid phthalate is heated. monium, so as to form tetraphthalimidoanthraquinone, which is then hydrolyzed.
The reaction for the formation of tetraphthalimidoanthraquinone is preferably carried out in a medium based on phthalic anhydride. According to a very simple embodiment of the process, a small amount of ammonia is added to phthalic anhydride and 1, 4, 5, 8 tetrachloranthraquinone is then added. These additions are made on phthalic anhydride, which is used in large excess and which serves as a reaction medium.
The quantities of water thus introduced are removed by heating at 150-180 '; at this point, the other reagents are added and the condensation proceeds to finally yield tetra-phthalimidoanthraquinone. The latter product is treated as usual with a hydrolyzing agent to give tetraminoanthraquinone.
Here are two examples of execution of the process of the invention Example <I> 1: </I> In a reaction vessel, 309 g of phthalic anhydride and 80 g of an ammonia solution are first introduced into 16% and heat at 150-1800 until the water vapors are removed, which can take about 2 to 3 hours. A mixture consisting of: 50 g tetrachloranthraquinone, 50 g potassium carbonate, and 0.5 g of powdered copper is then added to the melt thus obtained.
At this time, the temperature is brought to 225-230 C. After 18 hours of heating, the condensation is practically complete. The excess phthalic anhydride is extracted with boiling water and the resulting tetraphthalimido-anthraquinone is saponified with 400 g of sulfuric acid at 66 ", first at 40 C for 12 hours and, finally, at <B> 900 </B> for 1 hour. The reaction mass is precipitated in 15 l of water, the tetraminoanthraquinone sulfate is washed, then the base is liberated on the filter itself with a dilute solution. of soda ash.
Naturally, the final product can be dried as it is, or mixed before drying with products intended to facilitate its subsequent dispersion in the dye baths. Exesyaple <I> 2: </I> 131 g of ammonium acid phthalate and 200 g of phthalic anhydride are introduced into a reaction vessel, which are brought to fusion by heating at 150-1800.
A mixture consisting of: 50 g tetrachloranthraquinone, 50 g potassium carbonate, 0.5 g of powdered copper is then added to the melt thus obtained.
The whole is heated to 225-230 C for about 18 hours. The rest of the treatment is carried out as in Example 1.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR204855X | 1937-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH204855A true CH204855A (en) | 1939-05-31 |
Family
ID=8880295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH204855D CH204855A (en) | 1937-12-24 | 1938-04-21 | Process for the preparation of 1, 4, 5, 8 tetraminoanthraquinone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH204855A (en) |
-
1938
- 1938-04-21 CH CH204855D patent/CH204855A/en unknown
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