CN100422128C - Oxidation preparation method for 9- fluorenone compound from fluorine compound - Google Patents
Oxidation preparation method for 9- fluorenone compound from fluorine compound Download PDFInfo
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- CN100422128C CN100422128C CNB2006101022215A CN200610102221A CN100422128C CN 100422128 C CN100422128 C CN 100422128C CN B2006101022215 A CNB2006101022215 A CN B2006101022215A CN 200610102221 A CN200610102221 A CN 200610102221A CN 100422128 C CN100422128 C CN 100422128C
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Abstract
The invention discloses a preparing method of 9-fluorenone compound through oxidizing fluorene compound, which comprises the following steps: dissolving fluorene compound in the tetrahydrofuran; adding potassium hydroxide; setting the weight rate of fluorene compound and tetrahydrofuran at 1:4-6 with the molar rate of fluorene compound and potassium hydroxide at 1:0.5-2.5; stirring under normal temperature and pressure; oxidizing in the air; reacting for 1-8h; filtering; distilling; washing; drying; obtaining the product with producing rate at 98-99% and purity at 99-99.5%.
Description
Technical field
The present invention relates to aromatic compound, specifically belong to the method that a kind of compound of fluorene class oxidation prepares 9-Fluorenone compounds.
Background technology
9-Fluorenone compounds is the important intermediate raw material of synthetic fine chemicals, is widely used in the synthetic and preparation of dyestuff, photoconductive material, medicine and luminescent material.Mainly contain the following aspects about report by the method that the compound of fluorene class oxidation prepares 9-Fluorenone compounds both at home and abroad: Nippon Shokubai Co., Ltd's containing metal vanadium, titanium and alkali-metal catalyzer in 1996, adopt vapor phase process to prepare the 9-Fluorenone, temperature of reaction is more than 400 ℃, and productive rate is lower than 95%[ZL.96123084.3].Anshan Iron ﹠. Steel Group Corp in 2003 with vanadium-containing compound with contain the mixture of potassium, tin or titanium compound as catalyzer, method at 300-450 ℃ of following vapor phase process oxidation fluorenes prepares 9-Fluorenone [ZL.99112742.0]. and obviously above-mentioned two kinds of vapor phase process oxidation fluorenes prepare the method for 9-Fluorenone, complicated operation, the cost height.Shanghai Jiaohua Co., Ltd in 2006 with fluorenes with methyl-sulphoxide as solvent, sodium hydroxide is as catalyzer, temperature of reaction 50-100 ℃ with industrial oxygen prepared in reaction 9-Fluorenone, productive rate 96%[patent publication No. CN1754867A].The technology that the 9-Fluorenone is produced in the fluorenes liquid-phase oxidation of Te Kaiping 6-211729 Osaka, Japan gas Co., Ltd. is: fluorenes is in alkalescence or neutral solvent, add alkali and quaternary ammonium compound as phase-transfer catalyst, produce the 9-Fluorenone with atmospheric oxidation, productive rate 86.9% behind the purifying products, purity 99.0%.In above-mentioned two kinds of liquid phase preparation process, the former selects dimethyl sulfoxide (DMSO) boiling point height for use, recycling needs decompression distillation down (dimethyl sulfoxide (DMSO) Heating temperature greater than 90 ℃ time have decomposition), and reaction needed is heated to 50-100 ℃, and used oxygenant is an industrial oxygen; Latter's method is used phase-transfer catalyst in oxidising process, and productive rate is not high, obviously can increase the cost of product.Nineteen eighty-two, the Asahi Glass Co. of Japan reacted generation 2 with fluorenes and nitrogen bromo-succinimide (NBS) in acetic acid and in the Hydrogen bromide, 7-dibromo fluorenes, and then with 2,7-dibromo fluorenes is used CrO in acetic acid
3Oxidation preparation 2,7-two bromo-9-Fluorenones [JP 58,177,955,1983, Appl.82,160,409,13 Apr.1982].This method is with CrO
3As oxygenant, the cost height of product not only, and be unfavorable for environment protection.The abundant halls of department of chemistry of University Of Shanxi bear in 1989 wait people's [Shanxi chemical industry, 2,17,1989] and people [fuel and chemical industry such as the high Wei Min of Anshan Iron ﹠ Steel College in 1999,30 (2), 66,1999] reported with methyl-sulphoxide (DMSO) as solvent that potassium hydroxide is as catalyzer, 56 ℃ of temperature of reaction, the atmospheric oxidation fluorenes prepares the 9-Fluorenone, productive rate all is lower than 93%, by the product purity behind the recrystallization 99%, and the used dimethyl sulfoxide (DMSO) boiling point of this method height, add a large amount of water after the reaction and remove precipitated product, handle 10 times of waste water that contain DMSO and can bring bigger difficulty to solvent; Reaction process needs strict control reaction temperature, and the used solvent (alcohol, ether and benzene class) of recrystallization brings adverse influence to cost and environment protection.
Summary of the invention
In order to overcome the shortcoming of prior art, the object of the invention be to provide a kind of reaction conditions gentleness, easy and simple to handle, productive rate is high, cost is low, pollute the method that little compound of fluorene class oxidation prepares 9-Fluorenone compounds.
Compound of fluorene class oxidation provided by the invention prepares the method for 9-Fluorenone compounds, comprises the steps:
Compound of fluorene class is dissolved in the tetrahydrofuran (THF), adds potassium hydroxide then, the weight ratio that feeds intake of compound of fluorene class and tetrahydrofuran (THF) is 1: 4-6; The molar ratio of compound of fluorene class and potassium hydroxide is 1: 0.5-2.5; Stir under room temperature, condition of normal pressure, atmospheric oxidation was reacted 1-8 hour, filter, and distillation, washing, drying makes 9-Fluorenone compounds, productive rate 98-99%, purity 99-99.5%.Solvent after the present invention uses needn't be done further processing and promptly can be recycled.
When described compound of fluorene class was fluorenes, described 9-Fluorenone compounds was the 9-Fluorenone; Its preferred version: fluorenes is dissolved in the tetrahydrofuran (THF), adds potassium hydroxide then, the weight ratio that feeds intake of fluorenes and tetrahydrofuran (THF) is 1: 4-6; The molar ratio of fluorenes and potassium hydroxide is 1: 1-2.5; Stir under room temperature, condition of normal pressure, atmospheric oxidation was reacted 4-8 hour, filter, and distillation, washing, drying makes the 9-Fluorenone.
Described compound of fluorene class is 2, and during 7-dibromo fluorenes, described 9-Fluorenone compounds is 2,7-two bromo-9-Fluorenones; Its preferred version: with 2,7-dibromo fluorenes is dissolved in the tetrahydrofuran (THF), adds potassium hydroxide then, and 2, the weight ratio that feeds intake of 7-dibromo fluorenes and tetrahydrofuran (THF) is 1: 4-6; 2, the molar ratio of 7-dibromo fluorenes and potassium hydroxide is 1: 0.5-2; Stir under room temperature, condition of normal pressure, atmospheric oxidation was reacted 1-3 hour, filter, and distillation, washing, drying makes 2,7-two bromo-9-Fluorenones.
Described compound of fluorene class is 2, and during 7-dinitrobenzene fluorenes, described 9-Fluorenone compounds is 2,7-dinitrobenzene-9-Fluorenone; Its preferred version: with 2,7-dinitrobenzene fluorenes is dissolved in the tetrahydrofuran (THF), adds potassium hydroxide then, and 2, the weight ratio that feeds intake of 7-dinitrobenzene fluorenes and tetrahydrofuran (THF) is 1: 4-6; 2, the molar ratio of 7-dinitrobenzene fluorenes and potassium hydroxide is 1: 0.5-2; Stir under room temperature, condition of normal pressure, atmospheric oxidation was reacted 1-2 hour, filter, and distillation, washing, drying makes 2,7-dinitrobenzene-9-Fluorenone.
Described compound of fluorene class is 2, and during 7-dichloro fluorenes, described 9-Fluorenone compounds is 2,7-two chloro-9-Fluorenones; Its preferred version: with 2,7-dichloro fluorenes is dissolved in the tetrahydrofuran (THF), adds potassium hydroxide then, and 2, the weight ratio that feeds intake of 7-dichloro fluorenes and tetrahydrofuran (THF) is 1: 4-6; 2, the molar ratio of 7-dichloro fluorenes and potassium hydroxide is 1: 0.5-2; Stir under room temperature, condition of normal pressure, atmospheric oxidation was reacted 1-3 hour, filter, and distillation, washing, drying makes 2,7-two chloro-9-Fluorenones.
When described compound of fluorene class was 2-bromine fluorenes, described 9-Fluorenone compounds was a 2-bromo-9-Fluorenone; Its preferred version: 2-bromine fluorenes is dissolved in the tetrahydrofuran (THF), adds potassium hydroxide then, the weight ratio that feeds intake of 2-bromine fluorenes and tetrahydrofuran (THF) is 1: 4-6; The molar ratio of 2-bromine fluorenes and potassium hydroxide is 1: 0.5-2; Stir under room temperature, condition of normal pressure, atmospheric oxidation was reacted 2-3 hour, filter, and distillation, washing, drying makes 2-bromo-9-Fluorenone.
When described compound of fluorene class was the 2-nitrofluorene, described 9-Fluorenone compounds was 2-nitro-9-Fluorenone.Its preferred version: the 2-nitrofluorene is dissolved in the tetrahydrofuran (THF), adds potassium hydroxide then, the weight ratio that feeds intake of 2-nitrofluorene and tetrahydrofuran (THF) is 1: 4-6; The molar ratio of 2-nitrofluorene and potassium hydroxide is 1: 0.5-2; Stir under room temperature, condition of normal pressure, atmospheric oxidation was reacted 1-3 hour, filter, and distillation, washing, drying makes 2-nitro-9-Fluorenone.
Compared with prior art, reaction conditions gentleness of the present invention can be finished reaction under the room temperature normal pressure; Easy and simple to handle; Productive rate height (98-99%); Cost is low; Environmental pollution is little, and the solvent after the use needn't be done further processing and promptly can be recycled.
Embodiment
Reagent: fluorenes, analytical pure, the Long Huagongshijichang of Chengdu section; 2,7-dibromo fluorenes, synthetic by this research department, its structure is composed conclusive evidence by HNMR, IR; 2,7-dinitrobenzene fluorenes, analytical pure, Changzhou Wujin ring phoenix laboratory; 2,7-dichloro fluorenes, analytical pure, occasion chemical industry company limited is praised in Shanghai; 2-bromine fluorenes, analytical pure, the permanent International Trading Company Ltd of Shanghai Supreme Being; The 2-nitrofluorene, analytical pure, Shanghai Christian era company limited; Potassium hydroxide, analytical pure, new fine chemistry industry development centre, sky, Tianjin; Tetrahydrofuran (THF), analytical pure, huge chemical experimental factory, Tianjin.
Embodiment 1.1 fluorenes oxidations prepare the 9-Fluorenone
Operation steps: in being housed, reflux condensing tube and churned mechanically 250 milliliters of three-necked flasks add 20g fluorenes (0.12mol), 120 milliliters of tetrahydrofuran (THF)s, 6.70g potassium hydroxide (0.12mol) is opened and is stirred, and reaction is 6 hours under the room temperature.Reacting liquid filtering is removed potassium hydroxide, and filtrate is removed through distillation and washed with water three times after desolvating, and drying promptly obtains purity and be 99.0% 9-Fluorenone, yield 98.5%.
Embodiment 1.2 fluorenes oxidations prepare the 9-Fluorenone
Operation steps: in reflux condensing tube and churned mechanically 250 milliliters of three-necked flasks are housed, add 20g fluorenes (0.12mol), 100 milliliters of tetrahydrofuran (THF)s (go up example and use the back recovered solvent), 16.87g potassium hydroxide (0.3mol) is opened and stirred, reaction is 5 hours under the room temperature.Reacting liquid filtering is removed insolubles, and filtrate is removed through distillation and washed with water three times after desolvating, and drying promptly obtains purity and be 99.2% 9-Fluorenone, yield 99.1%.
The physical constant of 9-Fluorenone and spectral data:
The outward appearance of product: yellow solid; Fusing point: 83-85 ℃; IR (KBr) cm
-1: 3060,3050,1710,1602,1563,1433,1365,1324,1152,1099,1003,876,854,671,661; H
1NMR δ ppm:7.65 (d, 2H), 7.45-7.48 (m, 4H), 7.28 (d, 2H).
Embodiment 2.1 2,7-dibromo fluorenes oxidation preparation 2,7-two bromo-9-Fluorenones
Operation steps: in being housed, reflux condensing tube and churned mechanically 250 milliliters of three-necked flasks add 20g 2,7-dibromo fluorenes (0.06mol), 120 milliliters of tetrahydrofuran (THF)s, 1.68g potassium hydroxide (0.03mol) is opened and is stirred, and reaction is 2.5 hours under the room temperature.The reaction solution suction filtration is removed insolubles, and filtrate is removed through distillation and washed with water three times after desolvating, drying, promptly obtain purity and be 99.5% 2,7-two bromo-9-Fluorenones, yield 99.0%.
Embodiment 2.2 2,7-dibromo fluorenes oxidation preparation 2,7-two bromo-9-Fluorenones
Operation steps: in reflux condensing tube and churned mechanically 250 milliliters of three-necked flasks are housed, add 20g 2,7-dibromo fluorenes (0.06mol), 100 milliliters of tetrahydrofuran (THF)s (go up example and use the back recovered solvent), 6.70g potassium hydroxide (0.12mol), open and stir, reaction is 1.5 hours under the room temperature.Reacting liquid filtering is removed insolubles, and filtrate is removed through distillation and washed with water three times after desolvating, drying, promptly obtain purity and be 99.5% 2,7-two bromo-9-Fluorenones, yield 99.3%.
2, the physical constant and the spectral data of 7-two bromo-9-Fluorenones:
The outward appearance of product: yellow solid; Fusing point: 203-204 ℃; IR (KBr) cm
-1: 3080,3060,1742,1592,1505,1490,1410,1244,1090,826,780,688,472; H
1NMR δ ppm:7.83 (s, 2H), 7.65-7.68 (d, 2H), 7.38-7.40 (d, 2H).
Embodiment 3,2,7-dinitrobenzene fluorenes oxidation preparation 2,7-dinitrobenzene-9-Fluorenone
Operation steps: in being housed, reflux condensing tube and churned mechanically 250 milliliters of three-necked flasks add 20g2,7-dinitrobenzene fluorenes (0.078mol), 120 milliliters of tetrahydrofuran (THF)s, 2.18g potassium hydroxide (0.039mol) is opened and is stirred, and reaction is 1.5 hours under the room temperature.Reacting liquid filtering is removed potassium hydroxide, and filtrate is removed through distillation and washed with water three times after desolvating, drying, promptly obtain purity and be 99.5% 2,7-dinitrobenzene-9-Fluorenone, yield 99.1%.
2, the physical constant and the spectral data of 7-dinitrobenzene-9-Fluorenone:
The outward appearance of product: yellow solid; Fusing point: 293-295 ℃; IR (KBr) cm
-1: 3072,3054,1748,1610,1606,1520,1480,1430,1410,1340,1212,1162,930,846,790,742; H
1NMR δ ppm:8.26 (s, 2H), 7.92-7.94 (d, 2H), 7.44-7.46 (d, 2H).
Embodiment 4,2,7-dichloro fluorenes oxidation preparation 2,7-two chloro-9-Fluorenones
Operation steps: in being housed, reflux condensing tube and churned mechanically 250 milliliters of three-necked flasks add 20g2,7-dichloro fluorenes (0.085mol), 120 milliliters of tetrahydrofuran (THF)s, 7.15g potassium hydroxide (0.128mol) is opened and is stirred, and reaction is 2 hours under the room temperature.Reacting liquid filtering is removed potassium hydroxide, and filtrate is removed through distillation and washed with water three times after desolvating, drying, promptly obtain purity and be 99.2% 2,7-two chloro-9-Fluorenones, yield 98.9%.
2, the physical constant and the spectral data of 7-two chloro-9-Fluorenones:
The outward appearance of product: yellow solid; Fusing point: 193-195 ℃; IR (KBr) cm
-1: 3085,3065,1744,1602,1508,1502,1450,1408,1232,1010,810,772,695; H
1NMR δ ppm:7.98 (s, 2H), 7.71-7.73 (d, 2H), 7.40-7.42 (d, 2H).
Embodiment 5, the oxidation of 2-bromine fluorenes prepare 2-bromo-9-Fluorenone
Operation steps: in being housed, reflux condensing tube and churned mechanically 250 milliliters of three-necked flasks add 20g2-bromine fluorenes (0.082mol), 120 milliliters of tetrahydrofuran (THF)s, 4.57g potassium hydroxide (0.082mol) is opened and is stirred, and reaction is 3 hours under the room temperature.Reacting liquid filtering is removed potassium hydroxide, and filtrate is removed through distillation and washed with water three times after desolvating, and drying promptly obtains purity and be 99.4% 2-bromo-9-Fluorenone, yield 98.5%.
The physical constant and the spectral data of 2-bromo-9-Fluorenone:
The outward appearance of product: yellow solid; Fusing point: 147-148 ℃; IR (KBr) cm
-1: 3068,3050,1738,1502,1510,1460,1412,1300,1010,832,770,685,510; H
1NMR δ ppm:7.86 (s, 1H), 7.68-7.70 (d, 1H), 7.40-7.52 (m, 5H).
Embodiment 6, the oxidation of 2-nitrofluorene prepare 2-nitro-9-Fluorenone
Operation steps: in being housed, reflux condensing tube and churned mechanically 250 milliliters of three-necked flasks add 20g2-nitrofluorene (0.095mol), 120 milliliters of tetrahydrofuran (THF)s, 5.31g potassium hydroxide (0.095mol) is opened and is stirred, and reaction is 2 hours under the room temperature.Reacting liquid filtering is removed potassium hydroxide, and filtrate is removed through distillation and washed with water three times after desolvating, and drying promptly obtains purity and be 2-nitro-9-Fluorenone of 99.3%, yield 99.1%.
The physical constant and the spectral data of 2-nitro-9-Fluorenone:
The outward appearance of product: yellow solid; Fusing point: 223-225 ℃; IR (KBr) cm
-1: 3076,3062,1746,1606,1518,1492,1456,1408,1344,1210,1156,952,860,784,736; H
1NMR δ ppm:8.24 (s, 1H), 8.02-8.04 (d, 1H), 7.60-7.64 (m, 2H), 7.34-7.39 (m, 3H).
Claims (7)
1. the compound of fluorene class oxidation prepares the method for 9-Fluorenone compounds, it is characterized in that comprising the steps: compound of fluorene class is dissolved in the tetrahydrofuran (THF), adds potassium hydroxide then, and the weight ratio that feeds intake of compound of fluorene class and tetrahydrofuran (THF) is 1: 4-6; The molar ratio of compound of fluorene class and potassium hydroxide is 1: 0.5-2.5; Stir under room temperature, condition of normal pressure, atmospheric oxidation was reacted 1-8 hour, filter, and distillation, washing, drying makes 9-Fluorenone compounds.
2. prepare the method for 9-Fluorenone compounds according to the described compound of fluorene class oxidation of claim 1, it is characterized in that described compound of fluorene class is a fluorenes, the molar ratio of fluorenes and potassium hydroxide is 1: 1-2.5; Described 9-Fluorenone compounds is the 9-Fluorenone.
3. prepare the method for 9-Fluorenone compounds according to the described compound of fluorene class oxidation of claim 1, it is characterized in that described compound of fluorene class is 2,7-dibromo fluorenes, 2, the molar ratio of 7-dibromo fluorenes and potassium hydroxide is 1: 0.5-2; Described 9-Fluorenone compounds is 2,7-two bromo-9-Fluorenones.
4. prepare the method for 9-Fluorenone compounds according to the described compound of fluorene class oxidation of claim 1, it is characterized in that described compound of fluorene class is 2,7-dinitrobenzene fluorenes, 2, the molar ratio of 7-dinitrobenzene fluorenes and potassium hydroxide is 1: 0.5-2; Described 9-Fluorenone compounds is 2,7-dinitrobenzene-9-Fluorenone.
5. prepare the method for 9-Fluorenone compounds according to the described compound of fluorene class oxidation of claim 1, it is characterized in that described compound of fluorene class is 2,7-dichloro fluorenes, 2, the molar ratio of 7-dichloro fluorenes and potassium hydroxide is 1: 0.5-2; Described 9-Fluorenone compounds is 2,7-two chloro-9-Fluorenones.
6. the method for preparing 9-Fluorenone compounds according to the described compound of fluorene class oxidation of claim 1 is characterized in that described compound of fluorene class is a 2-bromine fluorenes, and the molar ratio of 2-bromine fluorenes and potassium hydroxide is 1: 0.5-2; Described 9-Fluorenone compounds is a 2-bromo-9-Fluorenone.
7. the method for preparing 9-Fluorenone compounds according to the described compound of fluorene class oxidation of claim 1 is characterized in that described compound of fluorene class is the 2-nitrofluorene, and the molar ratio of 2-nitrofluorene and potassium hydroxide is 1: 0.5-2; Described 9-Fluorenone compounds is 2-nitro-9-Fluorenone.
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Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101514160B (en) * | 2009-04-01 | 2012-06-27 | 山西大学 | Method for preparing 2, 7-dibromo-4-nitrofluorenone |
| CN101607878B (en) * | 2009-07-16 | 2013-03-13 | 邱孟杰 | Device for preparing fluorenone by means of liquid phase oxidation and preparation method thereof |
| CN102391129A (en) * | 2011-10-31 | 2012-03-28 | 中钢集团鞍山热能研究院有限公司 | Method for producing 2, 7-binitro fluorenone |
| CN103819347A (en) * | 2014-03-01 | 2014-05-28 | 张家港威胜生物医药有限公司 | Synthetic method of 2,7-diaminofluorene |
| CN104030907B (en) * | 2014-05-28 | 2016-08-31 | 沈阳化工研究院有限公司 | A kind of liquid phase oxidation prepares the method for 2-bromine Fluorenone |
| CN104030906A (en) * | 2014-05-28 | 2014-09-10 | 沈阳化工研究院有限公司 | Method for preparing 9-fluorenone by liquid-phase oxidation |
| CN108276261B (en) * | 2018-02-08 | 2021-01-05 | 新乡市润宇新材料科技有限公司 | Method for preparing 2-bromofluorenone by catalyzing molecular oxygen oxidation in aqueous phase |
| CN115611705A (en) * | 2021-07-14 | 2023-01-17 | 南京邮电大学 | Method for synthesizing fluorene tertiary alcohol |
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| FR2142217A5 (en) * | 1971-06-17 | 1973-01-26 | Elf Entr Rech Activit | Oxidation of substid aromatics - by oxygenin presence of acyclic polyethers |
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| WO1997045393A1 (en) * | 1996-05-24 | 1997-12-04 | The Dow Chemical Company | Process for making fluorenones |
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| FR2142217A5 (en) * | 1971-06-17 | 1973-01-26 | Elf Entr Rech Activit | Oxidation of substid aromatics - by oxygenin presence of acyclic polyethers |
| US4218400A (en) * | 1977-02-04 | 1980-08-19 | Rutgerswerke Aktiengesellschaft | Process for the production of fluorenone by catalytic oxidation of fluorene |
| WO1997045393A1 (en) * | 1996-05-24 | 1997-12-04 | The Dow Chemical Company | Process for making fluorenones |
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| 液相氧化法制取芴酮的研究. 胡鑫，肖瑞华，赵雪飞.鞍山钢铁学院学报，第25卷第6期. 2002 |
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Granted publication date: 20081001 Termination date: 20131128 |