CN104151239A - Synthesis method of pure 8-hydroxyquinoline aluminum salt - Google Patents
Synthesis method of pure 8-hydroxyquinoline aluminum salt Download PDFInfo
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- CN104151239A CN104151239A CN201410366875.3A CN201410366875A CN104151239A CN 104151239 A CN104151239 A CN 104151239A CN 201410366875 A CN201410366875 A CN 201410366875A CN 104151239 A CN104151239 A CN 104151239A
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- hydroxyquinoline
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- XAIDAKZDWHHFGM-UHFFFAOYSA-N aluminum;quinolin-8-ol Chemical compound [Al].C1=CN=C2C(O)=CC=CC2=C1 XAIDAKZDWHHFGM-UHFFFAOYSA-N 0.000 title abstract 3
- 238000001308 synthesis method Methods 0.000 title abstract 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 238000000498 ball milling Methods 0.000 claims abstract description 16
- 239000000463 material Substances 0.000 claims abstract description 16
- 239000002994 raw material Substances 0.000 claims abstract description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000001291 vacuum drying Methods 0.000 claims abstract description 9
- 238000003746 solid phase reaction Methods 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 238000010189 synthetic method Methods 0.000 claims description 4
- 239000004411 aluminium Substances 0.000 claims 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 2
- 230000000740 bleeding effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 20
- 239000005725 8-Hydroxyquinoline Substances 0.000 abstract description 18
- 229960003540 oxyquinoline Drugs 0.000 abstract description 18
- MJWPFSQVORELDX-UHFFFAOYSA-K aluminium formate Chemical compound [Al+3].[O-]C=O.[O-]C=O.[O-]C=O MJWPFSQVORELDX-UHFFFAOYSA-K 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 11
- 239000002351 wastewater Substances 0.000 abstract description 4
- 238000003801 milling Methods 0.000 abstract 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 23
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 15
- 239000007791 liquid phase Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- 238000000227 grinding Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- 238000009388 chemical precipitation Methods 0.000 description 7
- 230000002194 synthesizing effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000005086 pumping Methods 0.000 description 4
- -1 aluminum 8-hydroxyquinoline Chemical compound 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 230000002411 adverse Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 230000009916 joint effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 238000010671 solid-state reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/30—Metal salts; Chelates
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
- Manufacture And Refinement Of Metals (AREA)
Abstract
Description
技术领域 technical field
本发明涉及一种纯8-羟基喹啉铝的合成方法，特别是涉及一种以甲酸铝为主要原料、固相法直接合成纯8-羟基喹啉铝的方法。 The present invention relates to a method for synthesizing pure 8-hydroxyquinoline aluminum, in particular to a method for directly synthesizing pure 8-hydroxyquinoline aluminum using aluminum formate as the main raw material by solid-phase method.
背景技术 Background technique
8-羟基喹啉铝是一种非常理想的绿色发光材料，具有良好的发光特性、成膜性和热稳定性，被广泛应用于有机电致发光器件中。不过，纯度大于95%的8-羟基喹啉铝，才能用作有机发光材料。目前，工业化合成8-羟基喹啉铝的方法是液相化学沉淀法。反应原料是8-羟基喹啉和无机铝盐，比如硫酸铝、氯化铝、硝酸铝等水溶性铝盐。一般合成程序是：首先，将铝盐溶于水，将8-羟基喹啉溶于有机溶剂，比如无水乙醇等；然后，在一定条件下将8-羟基喹啉的有机溶剂溶液滴加到铝盐的水溶液中；最后，反应完毕，抽滤、洗涤、干燥。在各种液相化学沉淀法合成8-羟基喹啉铝的反应体系中，最常见的液相体系是水—乙醇体系。由于反应体系中氧和水的共同作用，而引发8-羟基喹啉铝发生聚合反应等副反应，导致液相化学沉淀法合成的8-羟基喹啉铝纯度低（通常为75%～80%）、产率低。结果是，液相化学沉淀法不可能直接合成纯度在95%之上的8-羟基喹啉铝。因此，必须采用升华法或柱色谱法对液相化学沉淀法合成的8-羟基喹啉铝进行多次提纯，才能获得纯度高于95%的8-羟基喹啉铝以满足发光材料的要求。然而，升华法或柱色谱法提纯过程相当复杂，无法大批量生产。而且，为了提高产率，通常使沉淀剂8-羟基喹啉大大过量。由此可知，现有液相化学沉淀法纯8-羟基喹啉铝的合成方法，由于产率低、流程复杂、生产规模小等因素，必然导致生产成本高昂。因此，现有工业化合成8-羟基喹啉铝的方法，不仅生产成本高，而且排放含有8-羟基喹啉和有机溶剂的废水。 8-Hydroxyquinoline aluminum is a very ideal green light-emitting material, which has good light-emitting properties, film-forming properties and thermal stability, and is widely used in organic electroluminescent devices. However, only aluminum 8-hydroxyquinoline with a purity greater than 95% can be used as an organic light-emitting material. At present, the industrialized method for synthesizing 8-hydroxyquinoline aluminum is the liquid-phase chemical precipitation method. The reaction raw materials are 8-hydroxyquinoline and inorganic aluminum salts, such as water-soluble aluminum salts such as aluminum sulfate, aluminum chloride, and aluminum nitrate. The general synthesis procedure is: at first, aluminum salt is dissolved in water, and 8-hydroxyquinoline is dissolved in organic solvent, such as dehydrated alcohol etc.; Then, the organic solvent solution of 8-hydroxyquinoline is added dropwise under certain conditions In the aqueous solution of aluminum salt; Finally, after the reaction is completed, filter, wash and dry. Among the reaction systems for the synthesis of 8-hydroxyquinoline aluminum by various liquid phase chemical precipitation methods, the most common liquid phase system is the water-ethanol system. Due to the joint action of oxygen and water in the reaction system, side reactions such as polymerization of 8-hydroxyquinoline aluminum are triggered, resulting in low purity of 8-hydroxyquinoline aluminum synthesized by liquid phase chemical precipitation (usually 75% to 80%) ), low yield. As a result, it is impossible to directly synthesize aluminum 8-hydroxyquinoline with a purity above 95% by liquid-phase chemical precipitation. Therefore, the 8-hydroxyquinoline aluminum synthesized by the liquid phase chemical precipitation method must be purified multiple times by sublimation or column chromatography to obtain 8-hydroxyquinoline aluminum with a purity higher than 95% to meet the requirements of luminescent materials. However, the purification process by sublimation or column chromatography is quite complicated and cannot be mass-produced. Furthermore, in order to increase the yield, the precipitating agent 8-hydroxyquinoline is usually used in large excess. It can be seen that the existing liquid-phase chemical precipitation method for the synthesis of pure 8-hydroxyquinoline aluminum will inevitably lead to high production costs due to factors such as low yield, complicated process, and small production scale. Therefore, the existing industrialized method for synthesizing 8-hydroxyquinoline aluminum not only has high production costs, but also discharges waste water containing 8-hydroxyquinoline and organic solvents.
发明内容 Contents of the invention
本发明的目的是针对现有工业化合成8-羟基喹啉铝的方法存在流程复杂、生产成本高、污染大的缺点，提出一种流程简短、生产成本低、污染小的合成8-羟基喹啉铝的新方法。 The purpose of the present invention is to propose a short process, low production cost, and less pollution for the synthesis of 8-hydroxyquinoline, which has the disadvantages of complex process, high production cost and large pollution in the existing industrialized method for synthesizing aluminum 8-hydroxyquinoline A new approach to aluminum.
本发明不采用液相反应体系，而是采用真空固相反应体系。通过固相反应消除了水对合成8-羟基喹啉铝的不良影响；通过抽真空消除了氧对合成8-羟基喹啉铝的不良影响。由于消除了水和氧引发的副反应，因此合成的8-羟基喹啉铝纯度高，纯度直接可以达到97%～99%。免除了液相化学沉淀法中复杂的多次提纯操作，可以降低生产成本。本发明通过机械力强化反应，反应原料8-羟基喹啉不需要过量，可以降低生产成本。合成流程简短，易于大规模直接生产纯度满足发光材料要求的纯8-羟基喹啉铝，可以降低生产成本。固相反应体系，既不使用水，也不使用有机溶剂，无废水排放，不仅可以保护环境，而且可以降低生产成本。 The present invention does not use a liquid phase reaction system, but a vacuum solid phase reaction system. The adverse effect of water on the synthesis of 8-hydroxyquinoline aluminum is eliminated by solid-state reaction; the adverse effect of oxygen on the synthesis of 8-hydroxyquinoline aluminum is eliminated by vacuuming. Due to the elimination of side reactions caused by water and oxygen, the synthesized 8-hydroxyquinoline aluminum has high purity, and the purity can directly reach 97% to 99%. The complex multiple purification operations in the liquid-phase chemical precipitation method are avoided, and the production cost can be reduced. The invention strengthens the reaction through mechanical force, and the reaction raw material 8-hydroxyquinoline does not need to be excessive, so that the production cost can be reduced. The synthesis process is short, and it is easy to directly produce pure 8-hydroxyquinoline aluminum whose purity meets the requirements of luminescent materials on a large scale, which can reduce the production cost. The solid-phase reaction system does not use water or organic solvents, and has no waste water discharge, which can not only protect the environment, but also reduce production costs.
本发明的反应原理为： The reaction principle of the present invention is:
Al(HCOO)3 + 3 C9H6NOH = Al(C9H6NO)3 + HCOOH Al(HCOO) 3 + 3 C 9 H 6 NOH = Al(C 9 H 6 NO) 3 + HCOOH
本发明一种纯8-羟基喹啉铝的合成方法，采用真空、固相反应体系，以8-羟基喹啉和甲酸铝为原料合成纯8-羟基喹啉铝，具体通过以下步骤来实现： A kind of synthetic method of pure 8-hydroxyquinoline aluminum of the present invention adopts vacuum, solid-phase reaction system, uses 8-hydroxyquinoline and aluminum formate as raw material to synthesize pure 8-hydroxyquinoline aluminum, specifically realizes through the following steps:
第一步，添加物料 The first step is to add materials
按照摩尔比为8-羟基喹啉:甲酸铝=3:1，将反应原料交替加入球磨罐中；研磨球为玛瑙球，研磨球与物料质量比为10:1～20:1。 According to the molar ratio of 8-hydroxyquinoline:aluminum formate=3:1, the reaction raw materials are alternately added to the ball milling tank; the grinding balls are agate balls, and the mass ratio of grinding balls to materials is 10:1-20:1.
第二步，球磨反应 The second step, ball milling reaction
球磨罐抽真空，真空度小于0.1 Pa后，停止抽气，开始球磨；球磨机转速为100 r/min～200 r/min，球磨时间为1 h～2 h，获得黄色产物。 Vacuumize the ball mill tank, and when the vacuum degree is less than 0.1 Pa, stop the pumping and start the ball mill; the ball mill speed is 100 r/min-200 r/min, the ball mill time is 1 h-2 h, and a yellow product is obtained.
第三步，真空干燥 The third step, vacuum drying
将第二步所得黄色产物置于真空干燥机中，于50 ℃下，真空干燥2 h，即得纯度为97%～99%的8-羟基喹啉铝。 Place the yellow product obtained in the second step in a vacuum dryer, and dry it in vacuum at 50 °C for 2 h to obtain 8-hydroxyquinoline aluminum with a purity of 97% to 99%.
本发明的优点是：1）无废水排放，保护环境。2）价格较高的反应原料8-羟基喹啉不需要过量。3）合成工艺流程短。4）8-羟基喹啉铝的产率高。5）生产成本低。6）真空干燥时，可以回收甲酸，反应原料的利用效率高。 The advantages of the invention are: 1) No waste water is discharged and the environment is protected. 2) 8-hydroxyquinoline, a relatively expensive reaction raw material, does not need to be in excess. 3) The synthesis process is short. 4) The yield of 8-hydroxyquinoline aluminum is high. 5) Low production cost. 6) During vacuum drying, formic acid can be recovered, and the utilization efficiency of reaction raw materials is high.
具体实施方式 Detailed ways
下面结合具体实施例对本发明所述的一种纯8-羟基喹啉铝的合成方法作进一步描述。 The synthetic method of a kind of pure 8-hydroxyquinoline aluminum of the present invention will be further described below in conjunction with specific examples.
实施例 1： Example 1 :
第一步，添加物料 The first step is to add materials
按照摩尔比为8-羟基喹啉:甲酸铝=3:1，将反应原料交替加入100 L球磨罐中，8-羟基喹啉总计加入6.438 kg，甲酸铝总计加入2.395 kg。研磨球为玛瑙球，研磨球与物料质量比为15:1，玛瑙球的质量为132.5 kg。 According to the molar ratio of 8-hydroxyquinoline:aluminum formate=3:1, the reaction raw materials were alternately added to a 100 L ball mill jar, 6.438 kg of 8-hydroxyquinoline and 2.395 kg of aluminum formate were added in total. The grinding balls are agate balls, the mass ratio of the grinding balls to the material is 15:1, and the mass of the agate balls is 132.5 kg.
第二步，球磨反应 The second step, ball milling reaction
球磨罐抽真空，真空度小于0.1 Pa后，停止抽气，开始球磨；球磨机转速为150 r/min，球磨时间为1.5 h，获得黄色产物。 Vacuum the ball mill tank, and when the vacuum degree is less than 0.1 Pa, stop the pumping and start the ball mill; the ball mill speed is 150 r/min, the ball mill time is 1.5 h, and a yellow product is obtained.
第三步，真空干燥 The third step, vacuum drying
将第二步所得黄色产物置于真空干燥机中，于50℃下，真空干燥2 h，即得纯度为98%的8-羟基喹啉铝。抽真空排出的气体含有甲酸，采用冷凝法回收甲酸。 Place the yellow product obtained in the second step in a vacuum dryer, and dry it in vacuum at 50 °C for 2 h to obtain 8-hydroxyquinoline aluminum with a purity of 98%. The gas discharged by vacuuming contains formic acid, and the formic acid is recovered by condensation.
实施例 2： Example 2 :
第一步，添加物料 The first step is to add materials
按照摩尔比为8-羟基喹啉:甲酸铝=3:1，将反应原料交替加入100 L球磨罐中，8-羟基喹啉总计加入9.657 kg，甲酸铝总计加入3.593 kg。研磨球为玛瑙球，研磨球与物料质量比为10:1，玛瑙球的质量为132.5 kg。 According to the molar ratio of 8-hydroxyquinoline:aluminum formate=3:1, the reaction raw materials were alternately added to a 100 L ball mill jar, 9.657 kg of 8-hydroxyquinoline and 3.593 kg of aluminum formate were added in total. The grinding ball is an agate ball, the mass ratio of the grinding ball to the material is 10:1, and the mass of the agate ball is 132.5 kg.
第二步，球磨反应 The second step, ball milling reaction
球磨罐抽真空，真空度小于0.1 Pa后，停止抽气，开始球磨；球磨机转速为200 r/min，球磨时间为1 h，获得黄色产物。 Vacuum the ball mill tank, and when the vacuum degree is less than 0.1 Pa, stop the pumping and start the ball mill; the ball mill speed is 200 r/min, the ball mill time is 1 h, and a yellow product is obtained.
第三步，真空干燥 The third step, vacuum drying
将第二步所得黄色产物置于真空干燥机中，于50℃下，真空干燥2 h，即得纯度为97%的8-羟基喹啉铝。抽真空排出的气体含有甲酸，采用冷凝法回收甲酸。 The yellow product obtained in the second step was placed in a vacuum dryer, and dried in vacuum at 50 °C for 2 h to obtain 8-hydroxyquinoline aluminum with a purity of 97%. The gas discharged by vacuuming contains formic acid, and the formic acid is recovered by condensation.
实施例 3： Example 3 :
第一步，添加物料 The first step is to add materials
按照摩尔比为8-羟基喹啉:甲酸铝=3:1，将反应原料交替加入100 L球磨罐中，8-羟基喹啉总计加入4.828 kg，甲酸铝总计加入1.797 kg。研磨球为玛瑙球，研磨球与物料质量比为20:1，玛瑙球的质量为132.5 kg。 According to the molar ratio of 8-hydroxyquinoline:aluminum formate=3:1, the reaction raw materials were alternately added to a 100 L ball mill jar, 4.828 kg of 8-hydroxyquinoline and 1.797 kg of aluminum formate were added in total. The grinding ball is an agate ball, the mass ratio of the grinding ball to the material is 20:1, and the mass of the agate ball is 132.5 kg.
第二步，球磨反应 The second step, ball milling reaction
球磨罐抽真空，真空度小于0.1 Pa后，停止抽气，开始球磨；球磨机转速为100 r/min，球磨时间为2 h，获得黄色产物。 Vacuum the ball mill tank, and when the vacuum degree is less than 0.1 Pa, stop the pumping and start ball milling; the ball mill speed is 100 r/min, the ball milling time is 2 h, and a yellow product is obtained.
第三步，真空干燥 The third step, vacuum drying
将第二步所得黄色产物置于真空干燥机中，于50℃下，真空干燥2 h，即得纯度为99%的8-羟基喹啉铝。抽真空排出的气体含有甲酸，采用冷凝法回收甲酸。 Place the yellow product obtained in the second step in a vacuum dryer, and dry it in vacuum at 50 °C for 2 h to obtain 8-hydroxyquinoline aluminum with a purity of 99%. The gas discharged by vacuuming contains formic acid, and the formic acid is recovered by condensation.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104649970A (en) * | 2015-02-09 | 2015-05-27 | 南昌航空大学 | Method for directly synthesizing organic luminous material, namely 8-hydroxyquinoline zinc |
| CN104744362A (en) * | 2015-04-08 | 2015-07-01 | 南昌航空大学 | Method for directly synthesizing pure copper 8-hydroxyquinoline |
| CN105237475A (en) * | 2015-11-23 | 2016-01-13 | 南昌航空大学 | Green synthesizing method for 8-hydroxyquinoline strontium |
| CN105348191A (en) * | 2015-11-30 | 2016-02-24 | 南昌航空大学 | Method for directly preparing pure 8-quinolinol calcium |
| CN105622504A (en) * | 2015-12-26 | 2016-06-01 | 南昌航空大学 | Environment-friendly method for preparing light-emitting material 8-barium hydroxyquinoline |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1212261A (en) * | 1998-04-08 | 1999-03-31 | 新疆大学 | Method for preparing nano material by solid phase chemical reaction |
| CN103145614A (en) * | 2013-03-11 | 2013-06-12 | 新疆大学 | Method for preparing 8-hydroxyquinoline magnesium nano sheet by room-temperature solid-state chemical reaction |
-
2014
- 2014-07-30 CN CN201410366875.3A patent/CN104151239B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1212261A (en) * | 1998-04-08 | 1999-03-31 | 新疆大学 | Method for preparing nano material by solid phase chemical reaction |
| CN103145614A (en) * | 2013-03-11 | 2013-06-12 | 新疆大学 | Method for preparing 8-hydroxyquinoline magnesium nano sheet by room-temperature solid-state chemical reaction |
Non-Patent Citations (3)
| Title |
|---|
| 朱凌健等: "高纯8-羟基喹啉铝的简便合成方法", 《化学试剂》, vol. 26, no. 6, 30 June 2004 (2004-06-30), pages 369 - 370 * |
| 贾梦鑫等: "8－羟基喹啉铝的制备与应用的研究进展", 《广州化工》, vol. 41, no. 23, 31 December 2013 (2013-12-31) * |
| 陈杰等: "8-羟基喹啉铝晶体的制备与表征", 《湖北汽车工业学院学报》, vol. 24, no. 2, 30 June 2010 (2010-06-30) * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104649970A (en) * | 2015-02-09 | 2015-05-27 | 南昌航空大学 | Method for directly synthesizing organic luminous material, namely 8-hydroxyquinoline zinc |
| CN104744362A (en) * | 2015-04-08 | 2015-07-01 | 南昌航空大学 | Method for directly synthesizing pure copper 8-hydroxyquinoline |
| CN105237475A (en) * | 2015-11-23 | 2016-01-13 | 南昌航空大学 | Green synthesizing method for 8-hydroxyquinoline strontium |
| CN105348191A (en) * | 2015-11-30 | 2016-02-24 | 南昌航空大学 | Method for directly preparing pure 8-quinolinol calcium |
| CN105622504A (en) * | 2015-12-26 | 2016-06-01 | 南昌航空大学 | Environment-friendly method for preparing light-emitting material 8-barium hydroxyquinoline |
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