CN103073397A - Preparation method of 2,3,6,7,10,11-hexahydroxy triphenylene - Google Patents
Preparation method of 2,3,6,7,10,11-hexahydroxy triphenylene Download PDFInfo
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Abstract
The invention relates to a preparation method of 2,3,6,7,10,11-hexahydroxy triphenylene, which comprises the following steps of: Step 1, preparing tripoly o-dimethoxybenzene, Step 2, adding tripoly o-dimethoxybenzene into N-methyl pyrrolidone, Step 3, adding a certain amount of sodium sulfide while stirring, Step 4, heating to certain temperature, Step 5,stirring at the constant temperature, Step 6, cooling, Step 7, adding a certain amount of deionized water, Step 8, using hydrochloric acid to adjust a pH (potential of hydrogen) value, separating a precipitate out, filtering, Step 9, dissolving a filter residue in a certain amount of tetrahydrofuran, dropwise adding methylene chloride at a certain proportion, separating a precipitate out, filtering, and Step 10, obtaining a white solid, and drying to obtain 2,3,6,7,10,11-hexahydroxy triphenylene. 2,3,6,7,10,11-hexahydroxy triphenylene prepared by the preparation method is the white solid, the appearance is attractive, and the purity is greater than 99%.
Description
Technical field
The present invention relates to a kind of 2,3,6,7,10, the preparation method of 11-hexahydroxy-benzo phenanthrene.
Background technology
The compound that is comprised of three phenyl ring is to separate from the lysate of benzene the earliest, and at first be referred to as benzophenanthrene (triphenybene) by Schultz, benzophenanthrene is because its special structure, make it that good optics and electric property be arranged, at present along with the breakthrough at optoelectronic areas of organic, polymer, benzophenanthrene and derivative thereof more and more receive publicity.
2,3,6,7,10,11-hexahydroxy-benzo is luxuriant and rich with fragrance, is a kind of important intermediate in the synthetic triphenylene, traditionally, can pyrocatechol be made or reduce quinone by transistion metal compound (such as iron trichloride) to form (such as the open NO.1993/118642 of the patent of Japanese unexamined), yet the product purity that obtains be not high, color is black, and outward appearance is very poor.
Therefore, invent a kind of newly 2,3,6,7,10, the preparation method of 11-hexahydroxy-benzo phenanthrene improves purity and the outward appearance of product, is the task of top priority in fact.
Summary of the invention
The technical problem to be solved in the present invention is: overcome that traditional preparation method makes 2,3,6, the defective that 7,10,11-hexahydroxy-benzo phenanthrene is black, appearance poor, purity is low, preparation method of the present invention make 2,3,6,7,10,11-hexahydroxy-benzo is luxuriant and rich with fragrance, it is white solid, purity〉99%, the product purity that makes than traditional method is higher, and outward appearance is also attractive in appearance.
In order to solve the problems of the technologies described above, the present invention proposes following technical scheme: a kind of 2,3,6,7,10, and the preparation method of 11-hexahydroxy-benzo phenanthrene, it comprises the steps:
Step 1: preparation trimerization 1,2-dimethoxy benzene;
Step 2: the trimerization 1,2-dimethoxy benzene is joined in the N-Methyl pyrrolidone;
Step 3: under stirring, add a certain amount of sodium sulphite;
Step 4: be heated to certain temperature;
Step 5: constant temperature stirs;
Step 6: cooling;
Step 7: add a certain amount of deionized water;
Step 8: regulate pH value with hydrochloric acid, separate out precipitation, filter;
Step 9: filter residue is dissolved in a certain amount of tetrahydrofuran (THF), drips a certain proportion of methylene dichloride, separates out precipitation, filters;
Step 10: obtain white solid, it is luxuriant and rich with fragrance that drying can obtain 2,3,6,7,10,11-hexahydroxy-benzo.
The further restriction of technique scheme is, in the above-mentioned steps 1, the method for preparing the trimerization 1,2-dimethoxy benzene is as follows: in ethylene dichloride, add Vanadium Pentoxide in FLAKES, the vitriol oil, iron trichloride, stir; Ice bath under the nitrogen protection, drips 1,2-dimethoxy benzene, dropwises stirring at room 24 hours; Be poured into water, tell the ethylene dichloride layer, drying, evaporate to dryness, the solid that obtains is the trimerization 1,2-dimethoxy benzene.
The further restriction of technique scheme is, in the above-mentioned steps 2, the part by weight of trimerization 1,2-dimethoxy benzene and N-Methyl pyrrolidone is 1:3～1:20, preferably 1:8～1:12.
The further restriction of technique scheme is, in the above-mentioned steps 3, the part by weight of trimerization 1,2-dimethoxy benzene and sodium sulphite is 1:3～1:10, preferably 1:5.
The further restriction of technique scheme is, in the above-mentioned steps 4, temperature is 100-160 ℃, preferred 120～140 ℃.
The further restriction of technique scheme is, in the above-mentioned steps 5, and 5～30 hours time that constant temperature stirs, preferred 10～15 hours.
The further restriction of technique scheme is, in the above-mentioned steps 7, the part by weight of trimerization 1,2-dimethoxy benzene and deionized water is 1:50～1:300, preferred 1:90～1:110.
The further restriction of technique scheme is, in the above-mentioned steps 8, regulates pH value and reaches 2～6, preferred 3～5.
The further restriction of technique scheme is, in the above-mentioned steps 9, the part by weight of trimerization 1,2-dimethoxy benzene and tetrahydrofuran (THF) is 1:5～1:30, preferred 1:8～1:12, the part by weight of tetrahydrofuran (THF) and methylene dichloride is 1:5～1:20, preferred 1:10～1:12.
The further restriction of technique scheme is, in the above-mentioned steps 10, drying mode is vacuum-drying.
Compared with prior art, the present invention has following beneficial effect: preparation method of the present invention make 2,3,6,7,10,11-hexahydroxy-benzo is luxuriant and rich with fragrance, is white solid, purity〉99%, the product purity that makes than traditional method is higher, outward appearance is also attractive in appearance.
Embodiment
It is a kind of 2,3,6,7,10 that the present invention proposes, and the preparation method of 11-hexahydroxy-benzo phenanthrene comprises the steps:
Step 1: preparation trimerization 1,2-dimethoxy benzene;
In the above-mentioned steps 1, the method for preparing the trimerization 1,2-dimethoxy benzene is as follows: in ethylene dichloride, add Vanadium Pentoxide in FLAKES, the vitriol oil, iron trichloride, stir; Ice bath under the nitrogen protection, drips 1,2-dimethoxy benzene, dropwises stirring at room 24 hours; Be poured into water, tell the ethylene dichloride layer, drying, evaporate to dryness, the solid that obtains is the trimerization 1,2-dimethoxy benzene;
Step 2: the trimerization 1,2-dimethoxy benzene is joined in the N-Methyl pyrrolidone;
In the above-mentioned steps 2, the part by weight of trimerization 1,2-dimethoxy benzene and N-Methyl pyrrolidone is 1:3～1:20, preferably 1:8～1:12;
Step 3: under stirring, add a certain amount of sodium sulphite;
In the above-mentioned steps 3, the part by weight of trimerization 1,2-dimethoxy benzene and sodium sulphite is 1:3～1:10, preferably 1:5;
Step 4: be heated to certain temperature;
In the above-mentioned steps 4, temperature is 100-160 ℃, preferred 120～140 ℃;
Step 5: constant temperature stirs;
In the above-mentioned steps 5,5～30 hours time that constant temperature stirs, preferred 10～15 hours;
Step 6: cool to room temperature;
Step 7: add a certain amount of deionized water;
In the above-mentioned steps 7, the part by weight of trimerization 1,2-dimethoxy benzene and deionized water is 1:50～1:300, preferred 1:90～1:110;
Step 8: regulate pH value with hydrochloric acid, separate out precipitation, filter;
In the above-mentioned steps 8, regulate pH value and reach 2～6, preferred 3～5;
Step 9: filter residue is dissolved in a certain amount of tetrahydrofuran (THF), drips the methylene dichloride of certainweight ratio, separates out precipitation, filters;
In the above-mentioned steps 9, the part by weight of trimerization 1,2-dimethoxy benzene and tetrahydrofuran (THF) is 1:5～1:30, preferred 1:8～1:12, and the part by weight of tetrahydrofuran (THF) and methylene dichloride is 1:5～1:20, preferred 1:10～1:12;
Step 10: obtain white solid, it is luxuriant and rich with fragrance that drying can obtain 2,3,6,7,10,11-hexahydroxy-benzo;
In the above-mentioned steps 10, drying mode is vacuum-drying.
The preparation of trimerization 1,2-dimethoxy benzene
In the 500ml ethylene dichloride, adding 10g Vanadium Pentoxide in FLAKES, the 10g vitriol oil delay, the 440g iron trichloride, stir.Ice bath under the nitrogen protection, drips the 70g 1,2-dimethoxy benzene, dropwises stirring at room 24 hours.Pour in the 3000ml water, tell the ethylene dichloride layer, drying, evaporate to dryness obtains the 50g solid, is the trimerization 1,2-dimethoxy benzene.
Preparation Example 1
Synthetic according to the method described above intermediate trimerization 1,2-dimethoxy benzene 10g is incorporated in the N-Methyl pyrrolidone of 100ml, stir lower, add sodium sulphite 60g, be heated to 130 ℃, constant temperature stirred 15 hours, was cooled to room temperature, added deionized water 1000ml and stirred, regulating pH value with hydrochloric acid is 4, separates out solid.Filter, take out filter residue.Filter residue adds the 100ml tetrahydrofuran (THF), and stirring and dissolving drips the 1000ml methylene dichloride, and crystallize out filters.The filter residue vacuum drying obtains white solid 6.3g, is 2,3,6,7,10,11-hexahydroxy-benzo luxuriant and rich with fragrance, purity〉99%.
Preparation Example 2
Synthetic according to the method described above intermediate trimerization 1,2-dimethoxy benzene 10g is incorporated in the N-Methyl pyrrolidone of 200ml, stir lower, add sodium sulphite 60g, be heated to 130 ℃, constant temperature stirred 15 hours, was cooled to room temperature, added deionized water 1000ml and stirred, regulating pH value with hydrochloric acid is 4, separates out solid.Filter, take out filter residue.Filter residue adds the 100ml tetrahydrofuran (THF), and stirring and dissolving drips the 1000ml methylene dichloride, and crystallize out filters.The filter residue vacuum drying obtains white solid 5.0g, is 2,3,6,7,10,11-hexahydroxy-benzo luxuriant and rich with fragrance, purity〉99%.
Preparation Example 3
Synthetic according to the method described above intermediate trimerization 1,2-dimethoxy benzene 10g is incorporated in the N-Methyl pyrrolidone of 100ml, stir lower, add sodium sulphite 30g, be heated to 130 ℃, constant temperature stirred 15 hours, was cooled to room temperature, added deionized water 1000ml and stirred, regulating pH value with hydrochloric acid is 4, separates out solid.Filter, take out filter residue.Filter residue adds the 100ml tetrahydrofuran (THF), and stirring and dissolving drips the 1000ml methylene dichloride, and crystallize out filters.The filter residue vacuum drying obtains white solid 6.1g, is 2,3,6,7,10,11-hexahydroxy-benzo luxuriant and rich with fragrance, purity〉99%.
Preparation Example 4
Synthetic according to the method described above intermediate trimerization 1,2-dimethoxy benzene 10g is incorporated in the N-Methyl pyrrolidone of 100ml, stir lower, add sodium sulphite 100g, be heated to 130 ℃, constant temperature stirred 15 hours, was cooled to room temperature, added deionized water 1000ml and stirred, regulating pH value with hydrochloric acid is 4, separates out solid.Filter, take out filter residue.Filter residue adds the 100ml tetrahydrofuran (THF), and stirring and dissolving drips the 1000ml methylene dichloride, and crystallize out filters.The filter residue vacuum drying obtains white solid 6.0g, is 2,3,6,7,10,11-hexahydroxy-benzo luxuriant and rich with fragrance, purity〉99%.
Preparation Example 5
Synthetic according to the method described above intermediate trimerization 1,2-dimethoxy benzene 10g is incorporated in the N-Methyl pyrrolidone of 100ml, stir lower, add sodium sulphite 60g, be heated to 130 ℃, constant temperature stirred 15 hours, was cooled to room temperature, added deionized water 500ml and stirred, regulating pH value with hydrochloric acid is 4, separates out solid.Filter, take out filter residue.Filter residue adds the 100ml tetrahydrofuran (THF), and stirring and dissolving drips the 1000ml methylene dichloride, and crystallize out filters.The filter residue vacuum drying obtains white solid 6.2g, is 2,3,6,7,10,11-hexahydroxy-benzo luxuriant and rich with fragrance, purity〉99%.
Preparation Example 6
Synthetic according to the method described above intermediate trimerization 1,2-dimethoxy benzene 10g is incorporated in the N-Methyl pyrrolidone of 100ml, stir lower, add sodium sulphite 60g, be heated to 130 ℃, constant temperature stirred 15 hours, was cooled to room temperature, added deionized water 3000ml and stirred, regulating pH value with hydrochloric acid is 4, separates out solid.Filter, take out filter residue.Filter residue adds the 100ml tetrahydrofuran (THF), and stirring and dissolving drips the 1000ml methylene dichloride, and crystallize out filters.The filter residue vacuum drying obtains white solid 6.3g, is 2,3,6,7,10,11-hexahydroxy-benzo luxuriant and rich with fragrance, purity〉99%.
Preparation Example 7
Synthetic according to the method described above intermediate trimerization 1,2-dimethoxy benzene 10g is incorporated in the N-Methyl pyrrolidone of 100ml, stir lower, add sodium sulphite 60g, be heated to 130 ℃, constant temperature stirred 15 hours, was cooled to room temperature, added deionized water 1000ml and stirred, regulating pH value with hydrochloric acid is 4, separates out solid.Filter, take out filter residue.Filter residue adds the 50ml tetrahydrofuran (THF), and stirring and dissolving drips the 1000ml methylene dichloride, and crystallize out filters.The filter residue vacuum drying obtains white solid 6.0g, is 2,3,6,7,10,11-hexahydroxy-benzo luxuriant and rich with fragrance, purity〉99%.
Preparation Example 8
Synthetic according to the method described above intermediate trimerization 1,2-dimethoxy benzene 10g is incorporated in the N-Methyl pyrrolidone of 100ml, stir lower, add sodium sulphite 60g, be heated to 130 ℃, constant temperature stirred 15 hours, was cooled to room temperature, added deionized water 1000ml and stirred, regulating pH value with hydrochloric acid is 4, separates out solid.Filter, take out filter residue.Filter residue adds the 300ml tetrahydrofuran (THF), and stirring and dissolving drips the 3000ml methylene dichloride, and crystallize out filters.The filter residue vacuum drying obtains white solid 5.0g, is 2,3,6,7,10,11-hexahydroxy-benzo luxuriant and rich with fragrance, purity〉99%.
Preparation Example 9
Synthetic according to the method described above intermediate trimerization 1,2-dimethoxy benzene 10g is incorporated in the N-Methyl pyrrolidone of 100ml, stir lower, add sodium sulphite 60g, be heated to 130 ℃, constant temperature stirred 15 hours, was cooled to room temperature, added deionized water 1000ml and stirred, regulating pH value with hydrochloric acid is 4, separates out solid.Filter, take out filter residue.Filter residue adds the 100ml tetrahydrofuran (THF), and stirring and dissolving drips the 500ml methylene dichloride, and crystallize out filters.The filter residue vacuum drying obtains white solid 6.1g, is 2,3,6,7,10,11-hexahydroxy-benzo luxuriant and rich with fragrance, purity〉99%.
Preparation Example 10
Synthetic according to the method described above intermediate trimerization 1,2-dimethoxy benzene 10g is incorporated in the N-Methyl pyrrolidone of 100ml, stir lower, add sodium sulphite 60g, be heated to 130 ℃, constant temperature stirred 15 hours, was cooled to room temperature, added deionized water 1000ml and stirred, regulating pH value with hydrochloric acid is 4, separates out solid.Filter, take out filter residue.Filter residue adds the 100ml tetrahydrofuran (THF), and stirring and dissolving drips the 2000ml methylene dichloride, and crystallize out filters.The filter residue vacuum drying obtains white solid 5.6g, is 2,3,6,7,10,11-hexahydroxy-benzo luxuriant and rich with fragrance, purity〉99%.
Preparation Example 11
Synthetic according to the method described above intermediate trimerization 1,2-dimethoxy benzene 10g is incorporated in the 50ml N-Methyl pyrrolidone, stir lower, add sodium sulphite 50g, be heated to 160 ℃, constant temperature stirred 15 hours, was cooled to room temperature, added deionized water 1000ml and stirred, regulating pH value with hydrochloric acid is 4, separates out solid.Filter, take out filter residue.Filter residue adds the 100ml tetrahydrofuran (THF), and stirring and dissolving drips 1000 ml methylene dichloride, and crystallize out filters.The filter residue vacuum drying obtains white solid 6.0g, is 2,3,6,7,10,11-hexahydroxy-benzo luxuriant and rich with fragrance, purity〉99%.
Preparation Example 12
Synthetic according to the method described above intermediate trimerization 1,2-dimethoxy benzene 10g is incorporated in the 100ml N-Methyl pyrrolidone, stir lower, add sodium sulphite 50g, be heated to 100 ℃, constant temperature stirred 15 hours, was cooled to room temperature, added deionized water 1000ml and stirred, regulating pH value with hydrochloric acid is 4, separates out solid.Filter, take out filter residue.Filter residue adds the 100ml tetrahydrofuran (THF), and stirring and dissolving drips 1000 ml methylene dichloride, and crystallize out filters.The filter residue vacuum drying obtains white solid 5.9g, is 2,3,6,7,10,11-hexahydroxy-benzo luxuriant and rich with fragrance, purity〉99%.
Preparation Example 13
Synthetic according to the method described above intermediate trimerization 1,2-dimethoxy benzene 10g is incorporated in the 100ml N-Methyl pyrrolidone, stir lower, add sodium sulphite 50g, be heated to 130 ℃, constant temperature stirred 15 hours, was cooled to room temperature, added deionized water 500ml and stirred, regulating pH value with hydrochloric acid is 6, separates out solid.Filter, take out filter residue.Filter residue adds the 100ml tetrahydrofuran (THF), and stirring and dissolving drips 1000 ml methylene dichloride, and crystallize out filters.The filter residue vacuum drying obtains white solid 5.8g, is 2,3,6,7,10,11-hexahydroxy-benzo luxuriant and rich with fragrance, purity〉99%.
Preparation Example 14
Synthetic according to the method described above intermediate trimerization 1,2-dimethoxy benzene 10g is incorporated in the 100ml N-Methyl pyrrolidone, stir lower, add sodium sulphite 50g, be heated to 130 ℃, constant temperature stirred 15 hours, was cooled to room temperature, added deionized water 1000ml and stirred, regulating pH value with hydrochloric acid is 2, separates out solid.Filter, take out filter residue.Filter residue adds the 50ml tetrahydrofuran (THF), and stirring and dissolving drips 500 ml methylene dichloride, and crystallize out filters.The filter residue vacuum drying obtains white solid 6.0g, is 2,3,6,7,10,11-hexahydroxy-benzo luxuriant and rich with fragrance, purity〉99%.
Preparation Example 15
Synthetic according to the method described above intermediate trimerization 1,2-dimethoxy benzene 10g is incorporated in the N-Methyl pyrrolidone of 100ml, stir lower, add sodium sulphite 60g, be heated to 130 ℃, constant temperature stirred 5 hours, was cooled to room temperature, added deionized water 1000ml and stirred, regulating pH value with hydrochloric acid is 4, separates out solid.Filter, take out filter residue.Filter residue adds the 100ml tetrahydrofuran (THF), and stirring and dissolving drips the 2000ml methylene dichloride, and crystallize out filters.The filter residue vacuum drying obtains white solid 5.0g, is 2,3,6,7,10,11-hexahydroxy-benzo luxuriant and rich with fragrance, purity〉99%.
Preparation Example 16
Synthetic according to the method described above intermediate trimerization 1,2-dimethoxy benzene 10g is incorporated in the N-Methyl pyrrolidone of 100ml, stir lower, add sodium sulphite 60g, be heated to 130 ℃, constant temperature stirred 30 hours, was cooled to room temperature, added deionized water 1000ml and stirred, regulating pH value with hydrochloric acid is 4, separates out solid.Filter, take out filter residue.Filter residue adds the 100ml tetrahydrofuran (THF), and stirring and dissolving drips the 2000ml methylene dichloride, and crystallize out filters.The filter residue vacuum drying obtains white solid 6.3g, is 2,3,6,7,10,11-hexahydroxy-benzo luxuriant and rich with fragrance, purity〉99%.
The present invention has following beneficial effect: preparation method of the present invention make 2,3,6,7,10,11-hexahydroxy-benzo is luxuriant and rich with fragrance, is white solid, purity〉99%, the product purity that makes than the method for tradition side is higher, outward appearance is also attractive in appearance.
Claims (10)
1. one kind 2,3,6,7,10, the preparation method of 11-hexahydroxy-benzo phenanthrene is characterized in that it comprises the steps:
Step 1: preparation trimerization 1,2-dimethoxy benzene;
Step 2: the trimerization 1,2-dimethoxy benzene is joined in the N-Methyl pyrrolidone;
Step 3: under stirring, add a certain amount of sodium sulphite;
Step 4: be heated to certain temperature;
Step 5: constant temperature stirs;
Step 6: cooling;
Step 7: add a certain amount of deionized water;
Step 8: regulate pH value with hydrochloric acid, separate out precipitation, filter;
Step 9: filter residue is dissolved in a certain amount of tetrahydrofuran (THF), drips a certain proportion of methylene dichloride, separates out precipitation, filters;
Step 10: obtain white solid, it is luxuriant and rich with fragrance that drying can obtain 2,3,6,7,10,11-hexahydroxy-benzo.
2. according to claim 1 a kind of 2,3,6,7, the preparation method of 10,11-hexahydroxy-benzo phenanthrene is characterized in that, in the above-mentioned steps 1, the method for preparing the trimerization 1,2-dimethoxy benzene is as follows: in ethylene dichloride, add Vanadium Pentoxide in FLAKES, the vitriol oil, iron trichloride, stir; Ice bath under the nitrogen protection, drips 1,2-dimethoxy benzene, dropwises stirring at room 24 hours; Be poured into water, tell the ethylene dichloride layer, drying, evaporate to dryness, the solid that obtains is the trimerization 1,2-dimethoxy benzene.
3. according to claim 1 a kind of 2,3,6,7,10, the preparation method of 11-hexahydroxy-benzo phenanthrene is characterized in that, in the above-mentioned steps 2, the part by weight of trimerization 1,2-dimethoxy benzene and N-Methyl pyrrolidone is 1:3～1:20, preferably 1:8～1:12.
4. according to claim 1 a kind of 2,3,6,7,10, the preparation method of 11-hexahydroxy-benzo phenanthrene is characterized in that, in the above-mentioned steps 3, the part by weight of trimerization 1,2-dimethoxy benzene and sodium sulphite is 1:3～1:10, preferably 1:5.
5. according to claim 1 a kind of 2,3,6,7,10, the preparation method of 11-hexahydroxy-benzo phenanthrene is characterized in that, in the above-mentioned steps 4, temperature is 100-160 ℃, preferred 120～140 ℃.
6. according to claim 1 a kind of 2,3,6,7,10, the preparation method of 11-hexahydroxy-benzo phenanthrene is characterized in that, in the above-mentioned steps 5, and 5～30 hours time that constant temperature stirs, preferred 10～15 hours.
7. according to claim 1 a kind of 2,3,6,7,10, the preparation method of 11-hexahydroxy-benzo phenanthrene is characterized in that, in the above-mentioned steps 7, the part by weight of trimerization 1,2-dimethoxy benzene and deionized water is 1:50～1:300, preferred 1:90～1:110.
8. according to claim 1 a kind of 2,3,6,7,10, the preparation method of 11-hexahydroxy-benzo phenanthrene is characterized in that, in the above-mentioned steps 8, regulates pH value and reaches 2～6, preferred 3～5.
9. according to claim 1 a kind of 2,3,6,7,10, the preparation method of 11-hexahydroxy-benzo phenanthrene is characterized in that, in the above-mentioned steps 9, the part by weight of trimerization 1,2-dimethoxy benzene and tetrahydrofuran (THF) is 1:5～1:30, preferred 1:8～1:12, the part by weight of tetrahydrofuran (THF) and methylene dichloride is 1:5～1:20, preferred 1:10～1:12.
10. according to claim 1 a kind of 2,3,6,7,10, the preparation method of 11-hexahydroxy-benzo phenanthrene is characterized in that, in the above-mentioned steps 10, drying mode is vacuum-drying.
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL70572A (en) * | 1983-12-28 | 1987-01-30 | Baruch Grunberger And Partners | Preparation of disc-shaped liquid crystals from the group of hexaalkoxy and hexaalkanoyloxy triphenylenes |
| JPH09118642A (en) * | 1995-08-21 | 1997-05-06 | Nippon Oil Co Ltd | Production of 2,3,6,7,10,11-hexahydroxytriphenylene |
| JP2005104870A (en) * | 2003-09-29 | 2005-04-21 | Fuji Photo Film Co Ltd | Method for producing 2,3,6,7,10,11-hexahydroxytriphenylene |
| TW200536820A (en) * | 2004-03-19 | 2005-11-16 | Otsuka Chemical Co Ltd | Crystal of hexahydroxytriphenylene monohydrate and method for preparation thereof |
| US20070093682A1 (en) * | 2003-10-22 | 2007-04-26 | Otsuka Chemical Co., Ltd. | Method for producing 2,3,6,7,10,11-hexahydroxytriphenylene |
| JP2007277101A (en) * | 2006-04-03 | 2007-10-25 | Daicel Chem Ind Ltd | Manufacturing method of 2,3,6,7,10,11-hexahydroxytriphenylene |
| CN101790504A (en) * | 2007-08-07 | 2010-07-28 | 和光纯药工业株式会社 | Process for producing triphenylene compound and crystal obtained by the process |
| CN101967147A (en) * | 2010-09-15 | 2011-02-09 | 陕西师范大学 | S-triazacoronene compound and synthesis method and application thereof |
-
2013
- 2013-01-28 CN CN201310031520.4A patent/CN103073397B/en active Active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL70572A (en) * | 1983-12-28 | 1987-01-30 | Baruch Grunberger And Partners | Preparation of disc-shaped liquid crystals from the group of hexaalkoxy and hexaalkanoyloxy triphenylenes |
| JPH09118642A (en) * | 1995-08-21 | 1997-05-06 | Nippon Oil Co Ltd | Production of 2,3,6,7,10,11-hexahydroxytriphenylene |
| JP2005104870A (en) * | 2003-09-29 | 2005-04-21 | Fuji Photo Film Co Ltd | Method for producing 2,3,6,7,10,11-hexahydroxytriphenylene |
| US20070093682A1 (en) * | 2003-10-22 | 2007-04-26 | Otsuka Chemical Co., Ltd. | Method for producing 2,3,6,7,10,11-hexahydroxytriphenylene |
| TW200536820A (en) * | 2004-03-19 | 2005-11-16 | Otsuka Chemical Co Ltd | Crystal of hexahydroxytriphenylene monohydrate and method for preparation thereof |
| JP2007277101A (en) * | 2006-04-03 | 2007-10-25 | Daicel Chem Ind Ltd | Manufacturing method of 2,3,6,7,10,11-hexahydroxytriphenylene |
| CN101790504A (en) * | 2007-08-07 | 2010-07-28 | 和光纯药工业株式会社 | Process for producing triphenylene compound and crystal obtained by the process |
| CN101967147A (en) * | 2010-09-15 | 2011-02-09 | 陕西师范大学 | S-triazacoronene compound and synthesis method and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| DAVID R. BEATTIE,等: "Triphenylene Hexa-n-alkylcyclohexanoates: A New Series of Disclike Liquid Crystals", 《J. MATER. CHEM.》, vol. 2, no. 12, 31 December 1992 (1992-12-31) * |
| 毛华香,等: "含柔性侧链苯并菲衍生物合成研究的进展", 《有机化学》, vol. 26, no. 4, 27 April 2006 (2006-04-27) * |
| 王又蓉: "《工业废水处理问答》", 31 January 2007, 国防工业出版社, article "工业废水处理问答" * |
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