CN103145687A - 2,11-disulfonic acid perylene anhydride and preparation method thereof - Google Patents
2,11-disulfonic acid perylene anhydride and preparation method thereof Download PDFInfo
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- CN103145687A CN103145687A CN2013100969896A CN201310096989A CN103145687A CN 103145687 A CN103145687 A CN 103145687A CN 2013100969896 A CN2013100969896 A CN 2013100969896A CN 201310096989 A CN201310096989 A CN 201310096989A CN 103145687 A CN103145687 A CN 103145687A
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Abstract
The invention relates to an anhydride and particularly relates to a 2,11-disulfonic acid perylene anhydride and a preparation method thereof; and the problem of low dyeing rate of anhydride dye is solved. The preparation method of the 2,11-disulfonic acid perylene anhydride comprises the following steps: adding the perylene anhydride into a container equipped with a stirrer and a thermometer; gradually dropwise adding a mixed acid solution of sulfuric acid and chlorosulfonic acid into the container, controlling the stirrer in the container to stir at a stirring velocity of 30-80 rpm (Revolutions Per Minute) and controlling the temperature of the reaction at minus 10 to 50 DEG C; stewing after reacting for 1-5 hours; transferring the stewed reactant into an alcohol solution and alcoholizing a solid substance; and filtering the solid substance, washing the solid substance by the alcohol substance, and drying to acquire the final product. The 2,11-disulfonic acid perylene anhydride produced by the method disclosed by the invention can be used as yellow dye and easily dissolved in water and organic solvents, has the advantage of high dyeing rate, is suitable for industrial promotion and can be used for solving the problem of low dyeing rate of the perylene anhydride dye.
Description
Technical field
She of the present invention is Ji perylene acid anhydride and its preparation method, be specially a kind of 2,11-Er Huang Suan perylene acid anhydride and preparation method thereof.
Background technology
The perylene acid anhydride is a kind of yellow dyes commonly used, and it is water insoluble, dissolve in organic solvent, but its solubleness is lower, only dissolves a few Ke De perylene acid anhydrides in 100 gram organic solvents, and the dye uptake of Shi De perylene acid anhydride dyestuff is low, hinders the popularization of perylene acid anhydride dyeing technique.
Summary of the invention
The present invention is for understanding the certainly low problem of perylene acid anhydride dyestuff dye uptake, provides a kind of 2,11-two sulphurs acid perylene acid anhydrides and preparation method thereof.
The present invention adopts following technical scheme to realize: a kind of 2, and 11-Er Huang Suan perylene acid anhydride, chemical structural formula is:
A kind of 2, the preparation method of 11-Er Huang Suan perylene acid anhydride comprises the following steps:
The perylene acid anhydride is added in the container that agitator and thermometer are housed;
The mix acid liquor that adds sulfuric acid and chlorsulfonic acid in the container is that 30～80 rev/mins, temperature of reaction reacted 1～5 hour under the condition of-10～50 ℃ in stir speed (S.S.), and is then standing;
Reactant after standing changes in alcohol solution, separates out solid matter;
Solid matter after filtration, after alcohols material washing, drying, obtain 2,11-Er Huang Suan perylene acid anhydride.
Present method make 2, Gan is the same with the perylene acid anhydride for 11-Er Huang Suan perylene, can be used as yellow dyes, and soluble in water, the solubleness in water is 237g, also can be dissolved in organic solvent, dye uptake is high, is beneficial to the popularization of dyeing; The sulfuric acid of selecting in present method and chlorsulfonic acid are that the researchist optimizes by test of many times, sulfuric acid, chlorsulfonic acid Neng He perylene anhydride reactant generate 2,11-Er Huang Suan perylene acid anhydride, and also found 2, the lower characteristic of 11-Er Huang Suan perylene acid anhydride solubleness in alcohol, make 2,11-Er Huang Suan perylene acid anhydride to separate out in alcohol.
Above-mentioned a kind of 2, the preparation method of 11-Er Huang Suan perylene acid anhydride, adding the speed of mix acid liquor in the container is 1～10ml/ minute, slowly drips acid solution, makes acid solution fully to react by He perylene acid anhydride.
Above-mentioned a kind of 2, the preparation method of 11-Er Huang Suan perylene acid anhydride, the concentration of the sulfuric acid in mix acid liquor are more than 60%, and the concentration of chlorsulfonic acid is beneficial to reaction and generates 2,11-Er Huang Suan perylene acid anhydride, and can or seldom not generate derived prods more than 10%.
Above-mentioned a kind of 2, the preparation method of 11-Er Huang Suan perylene acid anhydride, in mix acid liquor, the ratio of sulfuric acid and chlorsulfonic acid is 1:100～100:1, is beneficial to reaction and generates the finished product.
Above-mentioned a kind of 2, the preparation method of 11-Er Huang Suan perylene acid anhydride, described alcohol solution is the mixing solutions of methyl alcohol and ethanol, the ratio of methyl alcohol and ethanol is 1:10～10:1, can separate out greatly 2,11-Er Huang Suan perylene acid anhydride.
Above-mentioned a kind of 2, the preparation method of 11-Er Huang Suan perylene acid anhydride washs alcohols material used and is several that a kind of or arbitrary proportion in methyl alcohol, ethanol, propyl alcohol mixes, and methyl alcohol, ethanol, propyl alcohol washing effect are good, can not introduce other impurity, and the washing cost is also low.
The invention provides a kind of 2,11-Er Huang Suan perylene acid anhydride and its making method, 2,11-Er Huang Suan perylene acid anhydride can be used as yellow dyes, and it is soluble in water, also can be dissolved in organic solvent, and the solubleness in water is 237g, dye uptake is high, is suitable for industry and promotes, the low problem of Xie Jue perylene acid anhydride dyestuff dye uptake.
Description of drawings
Fig. 1 is the chemical structural formula of 2,11-Er Huang Suan perylene acid anhydride.
The chemical structural formula of figure 2 Wei perylene acid anhydrides.
Embodiment
Embodiment one:
200g perylene acid anhydride is added in the there-necked flask that agitator and thermometer are housed;
Adding concentration in dropping funnel is that 98% sulfuric acid and concentration are 10% chlorsulfonic acid 202ml, the ratio of sulfuric acid and chlorsulfonic acid is 100:1, dropping funnel adds mix acid liquor in container, and the speed that adds is 10ml/ minute, be that 80 rev/mins, temperature of reaction are reaction 1 hour under the condition of 50 ℃ in stir speed (S.S.), then standing;
Reactant after standing changes in the mixing solutions of methyl alcohol and ethanol, separates out solid matter, and in mixing solutions, the ratio of methyl alcohol and ethanol is 1:10;
Solid matter after filtration, after washing with alcohol, drying, obtain 2,11-Er Huang Suan perylene acid anhydride.
Embodiment two:
200g perylene acid anhydride is added in the there-necked flask that agitator and thermometer are housed;
Adding concentration in dropping funnel is that 80% sulfuric acid and concentration are 30% chlorsulfonic acid 202ml, the ratio of sulfuric acid and chlorsulfonic acid is 1:100, dropping funnel adds mix acid liquor in container, and the speed that adds is 5ml/ minute, be that 50 rev/mins, temperature of reaction are reaction 2 hours under the condition of 40 ℃ in stir speed (S.S.), then standing;
Reactant after standing changes in the mixing solutions of methyl alcohol and ethanol, separates out solid matter, and in mixing solutions, the ratio of methyl alcohol and ethanol is 10:1;
Solid matter after filtration, after methanol wash, drying, obtain 2,11-Er Huang Suan perylene acid anhydride.
Embodiment three:
200g perylene acid anhydride is added in the there-necked flask that agitator and thermometer are housed;
Adding concentration in dropping funnel is that 70% sulfuric acid and concentration are 45% chlorsulfonic acid 202ml, the ratio of sulfuric acid and chlorsulfonic acid is 1:10, dropping funnel adds mix acid liquor in container, and the speed that adds is 7.5ml/ minute, be that 60 rev/mins, temperature of reaction are reaction 3 hours under the condition of 0 ℃ in stir speed (S.S.), then standing;
Reactant after standing changes in the mixing solutions of methyl alcohol and ethanol, separates out solid matter, and in mixing solutions, the ratio of methyl alcohol and ethanol is 1:5;
Solid matter after filtration, after propyl alcohol washing, drying, obtain 2,11-Er Huang Suan perylene acid anhydride.
Embodiment four:
200g perylene acid anhydride is added in the there-necked flask that agitator and thermometer are housed;
Adding concentration in dropping funnel is that 60% sulfuric acid and concentration are 60% chlorsulfonic acid 202ml, the ratio of sulfuric acid and chlorsulfonic acid is 1:1, dropping funnel adds mix acid liquor in container, and the speed that adds is 1ml/ minute, stir speed (S.S.) be 30 rev/mins, temperature of reaction for reaction under the condition of-10 ℃ 5 hours, then standing;
Reactant after standing changes in the mixing solutions of methyl alcohol and ethanol, analyses to dissolve solid matter, and in mixing solutions, the ratio of methyl alcohol and ethanol is 2:1;
Solid matter after filtration, after the alcohol mixture liquid washing of methyl alcohol, ethanol and propyl alcohol, drying, obtain 2,11-Er Huang Suan perylene acid anhydride.
Embodiment five:
200g perylene acid anhydride is added in the there-necked flask that agitator and thermometer are housed;
Adding concentration in dropping funnel is that 75% sulfuric acid and concentration are 90% chlorsulfonic acid 202ml, the ratio of sulfuric acid and chlorsulfonic acid is 10:1, dropping funnel adds mix acid liquor in container, and the speed that adds is 6ml/ minute, be that 70 rev/mins, temperature of reaction are reaction 3.5 hours under the condition of 30 ℃ in stir speed (S.S.), then standing;
Reactant after standing changes in the mixing solutions of methyl alcohol and ethanol, analyses to dissolve solid matter, and in mixing solutions, the ratio of methyl alcohol and ethanol is 9:1;
Solid matter after filtration, after the alcohol mixture liquid washing of methyl alcohol and ethanol, drying, obtain 2,11-Er Huang Suan perylene acid anhydride.
Embodiment six:
200g perylene acid anhydride is added in the there-necked flask that agitator and thermometer are housed;
Adding concentration in dropping funnel is that 85% sulfuric acid and concentration are 75% chlorsulfonic acid 202ml, the ratio of sulfuric acid and chlorsulfonic acid is 50:1, dropping funnel adds mix acid liquor in container, and the speed that adds is 4ml/ minute, be that 40 rev/mins, temperature of reaction are reaction 4 hours under the condition of 20 ℃ in stir speed (S.S.), then standing;
Reactant after standing changes in the mixing solutions of methyl alcohol and ethanol, analyses to dissolve solid matter, and in mixing solutions, the ratio of methyl alcohol and ethanol is 7:1;
Solid matter after filtration, after the alcohol mixture liquid washing of propyl alcohol and ethanol, drying, obtain 2,11-Er Huang Suan perylene acid anhydride.
Embodiment seven:
200g perylene acid anhydride is added in the there-necked flask that agitator and thermometer are housed;
Adding concentration in dropping funnel is that 75% sulfuric acid and concentration are 50% chlorsulfonic acid 202ml, the ratio of sulfuric acid and chlorsulfonic acid is 80:1, dropping funnel adds mix acid liquor in container, and the speed that adds is 3ml/ minute, be that 65 rev/mins, temperature of reaction are reaction 4.5 hours under the condition of 10 ℃ in stir speed (S.S.), then standing;
Reactant after standing changes in the mixing solutions of methyl alcohol and ethanol, analyses to dissolve solid matter, and in mixing solutions, the ratio of methyl alcohol and ethanol is 5:1;
Solid matter after filtration, after the alcohol mixture liquid washing of methyl alcohol and propyl alcohol, drying, obtain 2,11-Er Huang Suan perylene acid anhydride.
Embodiment eight:
200g perylene acid anhydride is added in the there-necked flask that agitator and thermometer are housed;
Adding concentration in dropping funnel is that 90% sulfuric acid and concentration are 80% chlorsulfonic acid 202ml, the ratio of sulfuric acid and chlorsulfonic acid is 90:1, dropping funnel adds mix acid liquor in container, and the speed that adds is 2ml/ minute, be that 45 rev/mins, temperature of reaction are reaction 2.5 hours under the condition of 15 ℃ in stir speed (S.S.), then standing;
Reactant after standing changes in the mixing solutions of methyl alcohol and ethanol, analyses to dissolve solid matter, and in mixing solutions, the ratio of methyl alcohol and ethanol is 3:1;
Solid matter after filtration, after the alcohol mixture liquid washing of methyl alcohol and ethanol, drying, obtain 2,11-Er Huang Suan perylene acid anhydride.
Claims (10)
1. one kind 2,11-two sulphur acid perylene acid anhydrides is characterized in that chemical structural formula is:
。
2. one kind 2, the preparation method of 11-two sulphur acid perylene acid anhydrides is characterized in that comprising the following steps:
The perylene acid anhydride is added in the container that agitator and thermometer are housed;
The mix acid liquor that adds sulfuric acid and chlorsulfonic acid in the container is that 30～80 rev/mins, temperature of reaction reacted 1～5 hour under the condition of-10～50 ℃ in stir speed (S.S.), and is then standing;
Reactant after standing changes in alcohol solution, separates out solid matter;
Solid matter after filtration, after alcohols material washing, drying, obtain 2,11-Er Huang Suan perylene acid anhydride.
3. according to claim 2 a kind of 2, the preparation method of 11-Er Huang Suan perylene acid anhydride, the speed that it is characterized in that adding mix acid liquor in container be 1～10ml/minute.
4. according to claim 2 or 3 is described a kind of 2, and the preparation method of 11-Er Huang Suan perylene acid anhydride is characterized in that the concentration of the sulfuric acid in mix acid liquor more than 60%, and the concentration of chlorsulfonic acid is more than 10%.
5. according to claim 2 or 3 is described a kind of 2, and the preparation method of 11-Er Huang Suan perylene acid anhydride is characterized in that in mix acid liquor, the ratio of sulfuric acid and chlorsulfonic acid is 1:100～100:1.
6. according to claim 2 or 3 is described a kind of 2, and the preparation method of 11-Er Huang Suan perylene acid anhydride is characterized in that described alcohol solution is the mixing solutions of methyl alcohol and ethanol, and the ratio of methyl alcohol and ethanol is 1:10～10:1.
7. according to claim 2 or 3 is described a kind of 2, and the preparation method of 11-Er Huang Suan perylene acid anhydride is characterized in that washing alcohols material used and be several that a kind of or arbitrary proportion in methyl alcohol, ethanol, propyl alcohol mixes.
8. according to claim 4 a kind of 2, the preparation method of 11-Er Huang Suan perylene acid anhydride is characterized in that in mix acid liquor, the ratio of sulfuric acid and chlorsulfonic acid is 1:100～100:1.
9. according to claim 4 a kind of 2, the preparation method of 11-Er Huang Suan perylene acid anhydride is characterized in that described alcohol solution is the mixing solutions of methyl alcohol and ethanol, and the ratio of methyl alcohol and ethanol is 1:10～10:1.
10. according to claim 5 a kind of 2, the preparation method of 11-Er Huang Suan perylene acid anhydride is characterized in that described alcohol solution is the mixing solutions of methyl alcohol and ethanol, and the ratio of methyl alcohol and ethanol is 1:10～10:1.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994028073A1 (en) * | 1993-05-21 | 1994-12-08 | Russian Technology Group | Thermostable and lightfast dichroic light polarizers |
| CN1243511A (en) * | 1997-01-14 | 2000-02-02 | 西巴特殊化学品控股有限公司 | Preparation of -3,4-dicarboxylic anhydrides |
| CN101768369A (en) * | 2008-12-31 | 2010-07-07 | 大连理工大学 | Weather-resistance perylene imide dye and preparation method and application thereof |
-
2013
- 2013-03-26 CN CN2013100969896A patent/CN103145687A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994028073A1 (en) * | 1993-05-21 | 1994-12-08 | Russian Technology Group | Thermostable and lightfast dichroic light polarizers |
| CN1243511A (en) * | 1997-01-14 | 2000-02-02 | 西巴特殊化学品控股有限公司 | Preparation of -3,4-dicarboxylic anhydrides |
| CN101768369A (en) * | 2008-12-31 | 2010-07-07 | 大连理工大学 | Weather-resistance perylene imide dye and preparation method and application thereof |
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Application publication date: 20130612 |