CH130426A - A process for preparing a dye from the triarylmethane group. - Google Patents
A process for preparing a dye from the triarylmethane group.Info
- Publication number
- CH130426A CH130426A CH130426DA CH130426A CH 130426 A CH130426 A CH 130426A CH 130426D A CH130426D A CH 130426DA CH 130426 A CH130426 A CH 130426A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- hydrol
- preparing
- acid
- salt
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 2
- 239000003086 colorant Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 3
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- UWGCNDBLFSEBDW-UHFFFAOYSA-M sodium;4-[[4-(diethylamino)phenyl]-(4-diethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]naphthalene-2,7-disulfonate Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C2=CC=C(C=C2C=C(C=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 UWGCNDBLFSEBDW-UHFFFAOYSA-M 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé de préparation d'un colorant du groupe du triarylméthane. L'invention a trait à un perfectionnement apporté à la préparation du vert de lissa- mine V (index de colorants N 735) par condensation de p : p'-diaminobenzhydrol té- traéthylique et d'acide 2 : 7-naphtalènedisul- fonique.
Le procédé de préparation ordinaire com porte l'isolation de l'acide oméga-sulfonique de l'hydrol, qui étant soluble à la fois dans les acides et dans les alcalis, doit être pré cipité de solutions neutres.
Les inventeurs ont découvert maintenant que l'hydrol peut être obtenu sans aucune difficulté sous la forme de son sel avec l'acide 2 : 7-naphtalènedisulfonique par simple addition de 2:7-naphtalénedisulfonate de sodium à une solution de l'hydrol (obtenu par exemple par oxydation de tétraéthyledia- minodiph6nylméthane au moyen de per oxyde de plomb, à la manière ordinaire) et acidification du mélange.
Ce nouveau sel de l'hydrol peut être entièrement précipité dans les conditions indiquées ci-après et, comme il se dissout facilement dans l'acide sulfu rique concentré, la condensation en dérivé leucoïque du colorant peut être effectuée avan tageusement en faisant dissoudre le nouveau sel dans une solution d'acide sulfurique à 100 % et en faisant chauffer la solution. De cette manière l'isolation et la manipula tion de l'hydrol ou de son acide oméga-sul- fonique sont entièrement évitées, un autre avantage résidant dans le fait que l'acide naphtalènedisulfonique n'exige pas la dessic cation.
On va indiquer ci-après, à titre d'exem ple, un mode d'application de l'invention, dans lequel les parties sont indiquées en poids, étant entendu toutefois que cet exem ple n'est nullement limitatif.
<I>Exemple</I> 31 parties de p : p'-tétraéthylediaminodi- phénylméthane sont oxydées de la manière ordinaire au moyen de peroxyde de plomb pour en obtenir l'hydrol, le plomb étant éli miné à l'état de sulfate par addition de sul fate de sodium suivie d'un filtrage. On ajoute alors au filtrat la quantité de 2: 7 naphtalènedisulfonate de sodium correspon- pondant à 28,8 parties de l'acide libre, puis la quantité d'acide sulfurique voulue pour acidifier le tout (en général 5 parties par 100 parties de liqueur.
On laisse reposer le mélange 8 à 12 heures ; au bout de ce temps, la séparation étant achevée, on éli mine par filtration le naphtalènedisulfonate d'hydrol blanc cristallin ; on lave dans un peu d'eau et on fait sécher.
Pour effectuer la condensation, on fait dissoudre le produit, préparé de la ma nière indiquée, dans 125 parties d'acide sul furique à 100 % et on fait chauffer la solu= tion pendant 27 heures à une température de 98 à 100 C. Au bout de ce temps, on verse le mélange dans 830 parties d'eau ; et 3 à 4 heures après on recueille par filtration le leuco-dérivé du colorant et on lave dans l'eau.
Le composé leucoïque après oxydation, effectuée de la manière ordinaire au moyen du peroxyde de plomb, et après précipita- Lion avec du sel commun, donne un excellent rendement en colorant, après élimination du plomb à l'état de sulfate.
A process for preparing a dye from the triarylmethane group. The invention relates to an improvement in the preparation of lissamine green V (dye index N 735) by condensation of p: p'-diaminobenzhydrol tetraethyl and 2: 7-naphthalenedisulfonic acid.
The ordinary preparation process involves the isolation of omega-sulfonic acid from hydrol, which being soluble in both acids and alkalis, should be precipitated from neutral solutions.
The inventors have now discovered that hydrol can be obtained without any difficulty in the form of its salt with 2: 7-naphthalenedisulfonic acid by simple addition of sodium 2: 7-naphthalenedisulfonate to a solution of hydrol (obtained for example by oxidation of tetraethyldiaminodiph6nylmethane by means of lead peroxide, in the ordinary manner) and acidification of the mixture.
This new hydrol salt can be entirely precipitated under the conditions indicated below and, as it dissolves easily in concentrated sulfuric acid, the condensation into the leucoic derivative of the dye can be carried out advantageously by dissolving the new salt in a 100% sulfuric acid solution and heating the solution. In this way the isolation and handling of the hydrol or its omega-sulphonic acid is entirely avoided, another advantage being that the naphthalenedisulphonic acid does not require desiccation.
An embodiment of the invention will be indicated below by way of example, in which the parts are indicated by weight, it being understood, however, that this example is in no way limiting.
<I> Example </I> 31 parts of p: p'-tetraethylediaminodipenylmethane are oxidized in the ordinary manner by means of lead peroxide to obtain hydrol, the lead being eliminated in the sulphate state by addition of sodium sulfate followed by filtering. The amount of sodium 2: 7 naphthalenedisulfonate corresponding to 28.8 parts of the free acid is then added to the filtrate, followed by the amount of sulfuric acid desired to acidify the whole (generally 5 parts per 100 parts of liquor. .
The mixture is left to stand for 8 to 12 hours; at the end of this time, the separation being completed, the crystalline white hydrol naphthalenedisulfonate is removed by filtration; we wash in a little water and dry.
To effect the condensation, the product, prepared as indicated, is dissolved in 125 parts of 100% sulfuric acid and the solution is heated for 27 hours at a temperature of 98 to 100 C. At the end of this time, the mixture is poured into 830 parts of water; and 3-4 hours later, the leuco dye derivative is collected by filtration and washed in water.
The leucoic compound after oxidation, carried out in the usual manner by means of lead peroxide, and after precipitation with common salt, gives an excellent coloring yield after removal of lead in the sulphate state.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB130426X | 1927-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH130426A true CH130426A (en) | 1928-12-15 |
Family
ID=10015746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH130426D CH130426A (en) | 1927-02-05 | 1927-12-08 | A process for preparing a dye from the triarylmethane group. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH130426A (en) |
-
1927
- 1927-12-08 CH CH130426D patent/CH130426A/en unknown
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