CN101525282A - Method for preparing 2-bromo anthraquinone - Google Patents
Method for preparing 2-bromo anthraquinone Download PDFInfo
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- CN101525282A CN101525282A CN200910082510A CN200910082510A CN101525282A CN 101525282 A CN101525282 A CN 101525282A CN 200910082510 A CN200910082510 A CN 200910082510A CN 200910082510 A CN200910082510 A CN 200910082510A CN 101525282 A CN101525282 A CN 101525282A
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- bromo anthraquinone
- phenylformic acid
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- suction filtration
- bromobenzene
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Abstract
The invention discloses a method for preparing 2-bromo anthraquinone, comprising that bromobenzene and phthalic anhydride are reacted for 2-3 hours by being mixed at 40-50 DEG C with existence of anhydrous aluminum chloride,, thereby obtaining 2-(4-bromobenzeneacyl) phenylformic acid, wherein, quantity ratio of phthalic anhydride to bromobenzene to anhydrous aluminum chloride is 5:29:12. The 2-(4-bromobenzeneacyl) phenylformic acid is purified and then dissolved in concentrated sulfuric acid and temperature is raised gradually to 170 DEG C while mixing; and 2-bromo anthraquinone crude product is obtained by reaction. The 2-bromo anthraquinone crude product is cooled to 20-25 DEG C and then mixed with crushed ice; the mixture is stirred, filtered and washed. Toluol is used as solvent to carry out purification and active carbon is then used to carry out decoloring, then filtering and crystallizing are carried out, thereby obtaining 2-bromo anthraquinone. The invention can prepare 2-bromo anthraquinone in a relatively convenient way and has simple preparation method, simple operation and high yield and purity. The yield is 80-90% and the purity is higher than 98.5%.
Description
Technical field
The present invention relates to a kind of preparation method of anthracene derivative luminous organic material, be applicable to technical field of electronic materials.
Background technology
In the prior art, the production method of 2-bromo anthraquinone is a raw material with the 2-aminoanthraquinone normally, passes through after the diazotization and bromide reaction generation.This method cost of material is more expensive, and production method is numerous and diverse, and productive rate and purity are all lower.
Summary of the invention
Technical problem to be solved by this invention is, how under cheap, economic prerequisite, makes production method convenient and simple, and is easy to operate, and productive rate and purity are all higher, and a kind of method of the 2-of preparation bromo anthraquinone is provided.
Technical scheme of the present invention:
A kind of method for preparing the 2-bromo anthraquinone steps of the method are:
Step 1 is got the raw materials ready: Tetra hydro Phthalic anhydride bromobenzene Aluminum chloride anhydrous; Its feed ratio is 5: 29: 12 (mass ratio); Bromobenzene and Aluminum chloride anhydrous are joined in the reactor by feed ratio;
Step 2 when stirring, is pressed feed ratio and is added Tetra hydro Phthalic anhydride, and bromobenzene and Tetra hydro Phthalic anhydride react under 40～50 ℃ of conditions, and reaction times 2～3h obtains 2-(4-bromophenyl acyl) phenylformic acid;
Step 3, purifying: 2-(4-bromophenyl acyl) phenylformic acid is dissolved in the trash ice and stirs, suction filtration, the gained solid washes with water to neutrality; With 10% NAOH dissolving, at 20～25 ℃ of following suction filtrations, gained filtrate is regulated PH=1.0～2.0 with acid then, be settled out white solid, suction filtration, the white solid filter cake that obtains washes with water to neutrality, drying obtains purity and is 97%～98% 2-(4-bromophenyl acyl) phenylformic acid;
Step 4, it is in 98% the vitriol oil that above-mentioned 2-(4-bromophenyl acyl) phenylformic acid is dissolved in concentration, is warming up to 170 ℃ gradually when stirring, reaction 10～20min obtains 2-bromo anthraquinone crude product;
Step 5 is cooled to 20～25 ℃ with 2-bromo anthraquinone crude product, mixes with trash ice then, stirs suction filtration, washing;
Step 6 is carried out purifying with toluene as solvent, decolours with gac then, and suction filtration, crystallization obtains the 2-bromo anthraquinone.
Through nuclear magnetic resonance spectrum and high pressure liquid chromatography test proof products obtained therefrom is the 2-bromo anthraquinone.
The building-up process of 2-bromo anthraquinone is shown below:
The present invention compares the beneficial effect that is had with prior art:
Comparatively cheap, economical with method cost of material of the present invention;
Can prepare the 2-bromo anthraquinone with method of the present invention, production method is simple, and is easy to operate more conveniently, and productive rate and purity are all higher: productive rate is 80%～90%, purity＞98.5%; Fusing point (m.p.) is: 204 ℃～205 ℃.
Embodiment
The present invention will be further described below in conjunction with specific embodiment.
Embodiment one
A kind of method for preparing the 2-bromo anthraquinone is characterized in that, steps of the method are:
Step 1 is got bromobenzene 97.5 gram, Aluminum chloride anhydrous 40 grams join in the reactor;
Step 2 when stirring, adds Tetra hydro Phthalic anhydride 16.8 grams, and bromobenzene and Tetra hydro Phthalic anhydride react under 40 ℃ of conditions, and the reaction times is 3h, obtains 2-(4-bromophenyl acyl) phenylformic acid;
Step 3, purifying: 2-(4-bromophenyl acyl) phenylformic acid is dissolved in the trash ice and stirs, suction filtration, the gained solid washes with water to neutrality; With 10% NAOH dissolving, at 20 ℃ of following suction filtrations, gained filtrate is regulated PH=2.0 with 0.05mol/L hydrochloric acid then, be settled out white solid, suction filtration, the white solid filter cake that obtains washes with water to neutrality, drying obtains purity and is 97.5% 2-(4-bromophenyl acyl) phenylformic acid;
Step 4, it is in 98% the vitriol oil that above-mentioned 2-(4-bromophenyl acyl) phenylformic acid is dissolved in concentration, is warming up to 170 ℃ gradually when stirring, reaction 10min obtains 2-bromo anthraquinone crude product;
Step 5 is cooled to 20 ℃ with 2-bromo anthraquinone crude product, mixes with trash ice then, stirs suction filtration, washing;
Step 6 is carried out purifying with toluene as solvent, decolours with gac then, and suction filtration, crystallization gets the 2-bromo anthraquinone.
Productive rate is 90%.
Embodiment two
A kind of method for preparing the 2-bromo anthraquinone is characterized in that, steps of the method are:
Step 1 is got bromobenzene 146.25 gram, Aluminum chloride anhydrous 60 grams join in the reactor;
Step 2 when stirring, adds Tetra hydro Phthalic anhydride 25.2 grams, and bromobenzene and Tetra hydro Phthalic anhydride react under 50 ℃ of conditions, and the reaction times is 2h, obtains 2-(4-bromophenyl acyl) phenylformic acid;
Step 3, purifying: 2-(4-bromophenyl acyl) phenylformic acid is dissolved in the trash ice and stirs, suction filtration, the gained solid washes with water to neutrality; With 10% NAOH dissolving, at 25 ℃ of following suction filtrations, gained filtrate is regulated PH=1.0 with 0.1mol/L sulfuric acid then, be settled out white solid, suction filtration, the white solid filter cake that obtains washes with water to neutrality, drying obtains purity and is 97% 2-(4-bromophenyl acyl) phenylformic acid;
Step 4, it is in 98% the vitriol oil that above-mentioned 2-(4-bromophenyl acyl) phenylformic acid is dissolved in concentration, is warming up to 170 ℃ gradually when stirring, reaction 20min obtains 2-bromo anthraquinone crude product;
Step 5 is cooled to 25 ℃ with 2-bromo anthraquinone crude product, mixes with trash ice then, stirs suction filtration, washing;
Step 6 is carried out purifying with toluene as solvent, decolours with gac then, and suction filtration, crystallization gets the 2-bromo anthraquinone.
Productive rate is 83%.
Embodiment three
A kind of method for preparing the 2-bromo anthraquinone is characterized in that, steps of the method are:
Step 1 is got bromobenzene 585 gram, Aluminum chloride anhydrous 240 grams join in the reactor;
Step 2 when stirring, adds Tetra hydro Phthalic anhydride 100.8 grams, and bromobenzene and Tetra hydro Phthalic anhydride react under 45 ℃ of conditions, and the reaction times is 2.5h, obtains 2-(4-bromophenyl acyl) phenylformic acid;
Step 3, purifying: 2-(4-bromophenyl acyl) phenylformic acid is dissolved in the trash ice and stirs, suction filtration, the gained solid washes with water to neutrality; With 10% NAOH dissolving, at 23 ℃ of following suction filtrations, gained filtrate is regulated PH=1.5 with 0.2mol/L hydrochloric acid then, be settled out white solid, suction filtration, the white solid filter cake that obtains washes with water to neutrality, drying obtains purity and is 98% 2-(4-bromophenyl acyl) phenylformic acid;
Step 4, it is in 98% the vitriol oil that above-mentioned 2-(4-bromophenyl acyl) phenylformic acid is dissolved in concentration, is warming up to 170 ℃ gradually when stirring, reaction 18min obtains 2-bromo anthraquinone crude product;
Step 5 is cooled to 23 ℃ with 2-bromo anthraquinone crude product, mixes with trash ice then, stirs suction filtration, washing;
Step 6 is carried out purifying with toluene as solvent, decolours with gac then, and suction filtration, crystallization gets the 2-bromo anthraquinone.
Productive rate is 87%.
Embodiment four
A kind of method for preparing the 2-bromo anthraquinone is characterized in that, steps of the method are:
Step 1 is got bromobenzene 780 gram, Aluminum chloride anhydrous 320 grams join in the reactor;
Step 2 when stirring, adds Tetra hydro Phthalic anhydride 134.4 grams, and bromobenzene and Tetra hydro Phthalic anhydride react under 48 ℃ of conditions, and the reaction times is 2.3h, obtains 2-(4-bromophenyl acyl) phenylformic acid;
Step 3, purifying: 2-(4-bromophenyl acyl) phenylformic acid is dissolved in the trash ice and stirs, suction filtration, the gained solid washes with water to neutrality; With 10% NAOH dissolving, at 21.5 ℃ of following suction filtrations, gained filtrate is regulated PH=1.8 with 0.5mol/L phosphoric acid then, be settled out white solid, suction filtration, the white solid filter cake that obtains washes with water to neutrality, drying obtains purity and is 97.3% 2-(4-bromophenyl acyl) phenylformic acid;
Step 4, it is in 98% the vitriol oil that above-mentioned 2-(4-bromophenyl acyl) phenylformic acid is dissolved in concentration, is warming up to 170 ℃ gradually when stirring, reaction 12min obtains 2-bromo anthraquinone crude product;
Step 5 is cooled to 21.5 ℃ with 2-bromo anthraquinone crude product, mixes with trash ice then, stirs suction filtration, washing;
Step 6 is carried out purifying with toluene as solvent, decolours with gac then, and suction filtration, crystallization gets the 2-bromo anthraquinone.
Productive rate is 80%.
1HNMR(CDCl
3)，δ：7.8219(s，2H)；7.9181，7.9307(d，1H)；8.1683，8.1822(d，1H)；8.3132(s，2H)；8.8452(s，1H)。
Purity (purity)＞98.58% (HPLC).
Claims (1)
1. a method for preparing the 2-bromo anthraquinone is characterized in that, steps of the method are:
Step 1 is got the raw materials ready: Tetra hydro Phthalic anhydride bromobenzene Aluminum chloride anhydrous; Its feed ratio is 5: 29: 12 (mass ratio); Bromobenzene and Aluminum chloride anhydrous are joined in the reactor by feed ratio;
Step 2 when stirring, is pressed feed ratio and is added Tetra hydro Phthalic anhydride, and bromobenzene and Tetra hydro Phthalic anhydride react under 40～50 ℃ of conditions, and reaction times 2～3h obtains 2-(4-bromophenyl acyl) phenylformic acid;
Step 3, purifying: 2-(4-bromophenyl acyl) phenylformic acid is dissolved in the trash ice and stirs, suction filtration, the gained solid washes with water to neutrality; With 10% NAOH dissolving, at 20～25 ℃ of following suction filtrations, gained filtrate is regulated PH=1.0～2.0 with acid then, be settled out white solid, suction filtration, the white solid filter cake that obtains washes with water to neutrality, drying obtains purity and is 97%～98% 2-(4-bromophenyl acyl) phenylformic acid;
Step 4, it is in 98% the vitriol oil that above-mentioned 2-(4-bromophenyl acyl) phenylformic acid is dissolved in concentration, is warming up to 170 ℃ gradually when stirring, reaction 10～20min obtains 2-bromo anthraquinone crude product;
Step 5 is cooled to 20～25 ℃ with 2-bromo anthraquinone crude product, mixes with trash ice then, stirs suction filtration, washing;
Step 6 is carried out purifying with toluene as solvent, decolours with gac then, and suction filtration, crystallization obtains the 2-bromo anthraquinone.
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| Application Number | Priority Date | Filing Date | Title |
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| CN200910082510A CN101525282A (en) | 2009-04-24 | 2009-04-24 | Method for preparing 2-bromo anthraquinone |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102659551A (en) * | 2012-04-23 | 2012-09-12 | 张晗 | Preparation method of synthetic anthraquinone |
| CN102718644A (en) * | 2011-03-29 | 2012-10-10 | 上海引盛生物科技有限公司 | Preparation method for 2-bromoanthraquinone |
-
2009
- 2009-04-24 CN CN200910082510A patent/CN101525282A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102718644A (en) * | 2011-03-29 | 2012-10-10 | 上海引盛生物科技有限公司 | Preparation method for 2-bromoanthraquinone |
| CN102659551A (en) * | 2012-04-23 | 2012-09-12 | 张晗 | Preparation method of synthetic anthraquinone |
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