CN106366017A - Preparation method of 9-anthraldehyde-1, 1-diphenylhydrazone - Google Patents
Preparation method of 9-anthraldehyde-1, 1-diphenylhydrazone Download PDFInfo
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- CN106366017A CN106366017A CN201610682346.3A CN201610682346A CN106366017A CN 106366017 A CN106366017 A CN 106366017A CN 201610682346 A CN201610682346 A CN 201610682346A CN 106366017 A CN106366017 A CN 106366017A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/16—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of hydrazones
Abstract
The invention relates to a preparation method of 9-anthraldehyde-1, 1-diphenylhydrazone. The preparation method comprises that anthracene, phosphorous oxychloride and N, N-dimethyl formamide are added into a reaction container, the materials undergo a reaction at a temperature of 60-120 DEG C for 6-48h to produce 9-anthraldehyde, N-nitrosodiphenylamine, zinc, acetate acid gracial and an alcohol solvent are added into the reaction container, the mixture undergoes a reaction at a temperature of 0-40 DEG C for 1-9h to produce 1, 1-diphenylhydrazine, 9-anthraldehyde and 1, 1-diphenylhydrazine are added into the reaction container, the mixture undergoes a reaction, the reaction product is cooled and precipitated, and the crystals are filtered and then are recrystallized in benzene so that 9-anthraldehyde-1, 1-diphenylhydrazone is obtained. Through simple recrystallization of the desired compound, a product with purity greater than 99.5% is obtained. The preparation method has the advantages of low raw material cost, mild reaction conditions and high desired product yield. The preparation method provides possibility for use of the hydrazone compound as a semi-conducting material in research on organic electroluminescent devices and organic light conductors.
Description
Technical field
The invention belongs to synthesis chemical field is and in particular to 9- anthraldehyde -1,1- diphenyl hydrazone preparation method.
Background technology
Hydrazone compounds are the important hole mobile materials of a class, have excellent optical physicss and spectrochemical property.
With respect to other hole mobile materials, hydrazone compounds synthetic route is simple, compared with being easily purified, price relatively low.Hydrazone compounds exist
A series of field such as medicine, organic electroluminescence device, organic semiconducting materials and solaode has wide answering
Use prospect.
At present, in document, (biosensors and bioelectronics 2005,20:2353-2363) reports
The synthetic method of 9- anthraldehyde -1,1- diphenyl hydrazone.But employing expensive 1,1- hexichol hydrazine hydrochloride in document is
Raw material, is also added into expensive n in the reaction, and n- dipropyl ethamine is acid binding agent.The present invention develops simple to operate, safety
Reliability, high yield, 9- anthraldehyde -1 of low cost, 1- diphenyl hydrazone closes preparation method, and then is available for studying it in organic photoelectric
Various photoelectricity in sub- device and chemical property, have good realistic meaning.
Content of the invention
It is an object of the invention to provide a kind of new 9- anthraldehyde -1, the preparation method of 1- diphenyl hydrazone, it is easy to accomplish
Industrialization, products obtained therefrom purity height and steady quality.
The preparation method of the 9- anthraldehyde -1,1- diphenyl hydrazone of the present invention；Comprise the following steps:
(1) anthracene for 1:1:1-1:3:3 by mol ratio: phosphorus oxychloride: n, n- dimethylformamide adds in reaction vessel,
60-120 DEG C of reaction 6-48h generates 9- anthraldehyde；
(2) the n- nitrosodiphenylamine for 1:1:1-1:7:7 by mol ratio: zinc: glacial acetic acid adds reaction with alcohols solvent
In container, 0-40 DEG C of reaction 1-9h generates 1,1- hydrazo-benzene；
(3) the 9- anthraldehyde for 1:1.2-1:2 by mol ratio: 1,1- hydrazo-benzene adds in reaction vessel, 30-120 DEG C anti-
Should, stirring, cooling after reaction 12-48h has crystal to separate out, and after filtration, in benzene, recrystallization obtains product 9- anthraldehyde -1,1- hexichol
Base hydrazone.
Described step (1) anthracene, phosphorus oxychloride and n, the mol ratio of n- dimethylformamide is 1:1:1-1:3:3, preferably
Between 1:2:2-1:2.5:2.5.
Described step (1) response time is preferably 8-15h.
Described step (1) reaction temperature is preferably 90-120 DEG C.
The mol ratio of described step (2) n- nitrosodiphenylamine, zinc and glacial acetic acid is preferably 1:3:3-1:5:5.
Described step (2) response time is preferably 5-7h.
Described step (2) reaction temperature is preferably 16-40 DEG C.
The alcohols solvent of described step (2) is methanol, ethanol or n-butyl alcohol.
Described step (3) method according to claim 1 it is characterised in that: step (3) 9- anthraldehyde and n- are sub-
The mol ratio of nitrodiphenylamine is preferably 1:1.2-1:1.5.
Described step (3) reaction temperature is preferably 60-120 DEG C.
Described step (3) response time is preferably 20-28h.
Anthracene, phosphorus oxychloride and n in step (1) of the present invention, n- dimethylformamide low in raw material price, using commercially available product
Product.
After n- nitrosodiphenylamine in step (2) of the present invention is refined by the method for recrystallization, obtain yellow solid,
After reaction terminates, rapid filtration obtains the ethanol solution of 1,1- hydrazo-benzene, 1, the 1- hexichol that n- nitrosodiphenylamine is obtained after refining
The ethanol solution of hydrazine is light yellow liquid.
Preparation method of the present invention is raw material using the anthracene being easy to get and n- nitrosodiphenylamine, and through Weir, this Haake advanced in years is anti-
Answer, n- nitrosodiphenylamine reduces, aldehyde and hydrazine are condensed three-step reaction altogether, you can obtain target 9- anthraldehyde -1,1- diphenyl hydrazone
Compound.The target compound obtaining can obtain, through simple recrystallization, the product that purity is more than 99.5% (hplc).This
Bright have low raw-material cost, and reaction condition is gentle, experimental implementation safety, and post processing is simple, and target product yield is higher, purity
Also many advantages, such as very high.For synthesizing 9- anthraldehyde -1, the preparation of 1- diphenyl hydrazone compound provides new method, promotes
Hydrazone compounds are applied to organic electroluminescence device and organic light as semi-conducting material by the study on the synthesis of hydrazone compounds
The research of the aspects such as conductor provides more probabilities.
Brief description
Fig. 1 is the hplc spectrogram of the 9- anthraldehyde -1,1- diphenyl hydrazone that embodiment of the present invention one prepares.
Fig. 2 is the 9- anthraldehyde -1,1- diphenyl hydrazone that embodiment of the present invention one prepares1H-nmr spectrogram.
Specific embodiment
For a better understanding of the present invention, now specific embodiment is listed below, embodiment can be done into one to the present invention
The explanation of step and explanation, but the present invention is not limited to Examples below.
(1) anthracene for 1:1:1-1:3:3 by mol ratio: phosphorus oxychloride: n, n- dimethylformamide adds in reaction vessel,
60-120 DEG C of reaction 6-48h generates 9- anthraldehyde；
(2) mol ratio is the n- nitrosodiphenylamine of 1:1:1-1:7:7: zinc: glacial acetic acid and alcohols solvent add reaction to hold
In device, 0-40 DEG C of reaction 1-9h generates 1,1- hydrazo-benzene；
(3) the 9- anthraldehyde that (1) for 1:1.2-1:2 obtains by mol ratio: the product 1,1- hydrazo-benzene that (2) obtain adds
In reaction vessel, 30-120 DEG C of reaction, stirring, cooling after reaction 12-48h has crystal to separate out, and after filtration, in benzene, recrystallization obtains
Product 9- anthraldehyde -1,1- diphenyl hydrazone；Purity is more than 99.5% (hplc).
Embodiment 1:
(1) preparation of 9- anthraldehyde: equipped with reflux condensing tube, thermometer, Dropping funnel, four mouthfuls of mechanical agitator burnings
Bottle in, add phosphorus oxychloride (105ml, 1.12mol) and anthracene (200g, 1.12mol), open agitator and heating, be warmed up to
60 DEG C, dmf (80ml, 1.12mol) is added in Dropping funnel, completion of dropping in 1h.Then, after reaction 6h, cooling separates out
Crystal obtains product 188g, and fusing point is 104-105 DEG C.
(2) synthesis of 1,1- hydrazo-benzene: weigh the n- nitrosodiphenylamine that (198g, 1mol) refined and be added to 2.5l
Four-hole bottle in, and add the absolute methanol of 450ml, magnetic agitation, be subsequently adding (65g, 1mol) zinc powder, control temperature to be 0
DEG C, the glacial acetic acid of Deca (58ml, 1mol), drip and finish, sucking filtration after insulation reaction 1h, washs filter cake, merging filtrate is stand-by with methanol.
(3) synthesis of 9- anthraldehyde -1,1- diphenyl hydrazone: weigh the 9- anthracene first that (126g, 0.63mol) step (1) is obtained
In the four-hole bottle of 2.5l, 1, the 1- hydrazo-benzene filtrate that step (2) is obtained is added thereto aldehyde, and agitating heating maintains the temperature at
30 DEG C, after reaction 12h, filtered while hot, vacuum drying obtains yellow solid 200g, and yield is 88.0%.In benzene, recrystallization obtains
Product 9- anthraldehyde -1,1- diphenyl hydrazone, purity is 99.7% (hplc, spectrogram is as shown in Figure 1)；196-197 DEG C of fusing point,1H-nmr spectrogram as shown in Figure 2,1h nmr(400mhz,cdcl3) δ 8.45 (d, j=8.4hz, 2h), 8.36 (s, 1h), 8.23
(s, 1h), 8.00 7.87 (m, 2h), 7.45 (ddd, j=13.0,12.6,7.1hz, 8h), 7.35 (d, j=7.8hz, 4h),
7.22 (d, j=8.4hz, 2h).
In present embodiment, raw material anthracene and n- nitrosodiphenylamine are commercially available prod and to prepare product using open method equal
Can, reaction dissolvent is that commercially available analysis is pure, and distilled water used is laboratory from controlling the water circulation.
Present embodiment synthetic method is simple to operate, and low in raw material price is easy to get, and post processing saves time and saves trouble.
The synthetic route of present embodiment and 9- anthraldehyde -1,1- diphenyl hydrazone (tm) structure are as follows:
Embodiment 2:
(1) preparation of 9- anthraldehyde: equipped with reflux condensing tube, thermometer, Dropping funnel, four mouthfuls of mechanical agitator burnings
Bottle in, add phosphorus oxychloride (315ml, 3.36mol) and anthracene (200g, 1.12.36mol), open agitator and heating, heat up
To 80 DEG C, dmf (240ml, 3.36mol) is added in Dropping funnel, completion of dropping in 1h.Then after reaction 48h, cooling
Separate out crystal and obtain product 175g, fusing point is 104-105 DEG C.
(2) synthesis of 1,1- hydrazo-benzene: weigh the n- nitrosodiphenylamine that (198g, 1mol) refined and be added to 2.5l
Four-hole bottle in, and add the absolute methanol of 450ml, magnetic agitation, be subsequently adding (455g, 7mol) zinc powder, control the temperature to be
10 DEG C, the glacial acetic acid of Deca (406ml, 7mol), drip and finish, sucking filtration after insulation reaction 9h, washs filter cake, merging filtrate is treated with methanol
With.(3) synthesis of 9- anthraldehyde -1,1- diphenyl hydrazone: weigh (100g, 0.5mol) step (1) be obtained 9- anthraldehyde in
In the four-hole bottle of 2.5l, 1, the 1- hydrazo-benzene filtrate that step (2) is obtained is added thereto, and agitating heating maintains the temperature at 50 DEG C,
After reaction 48h, filtered while hot, vacuum drying obtains yellow solid 160g, and yield is 88.0%.
Embodiment 3:
(1) preparation of 9- anthraldehyde: equipped with reflux condensing tube, thermometer, Dropping funnel, four mouthfuls of mechanical agitator burnings
Bottle in, add phosphorus oxychloride (210ml, 2.24mol) and anthracene (200g, 1.12mol), open agitator and heating, be warmed up to
90 DEG C, dmf (160ml, 2.24mol) is added in Dropping funnel, completion of dropping in 1h.Then after reaction 8h, cooling analysis
Go out crystal and obtain product 200g, fusing point is 104-105 DEG C.
(2) synthesis of 1,1- hydrazo-benzene: weigh the n- nitrosodiphenylamine that (198g, 1mol) refined and be added to 2.5l
Four-hole bottle in, and add the absolute methanol of 450ml, magnetic agitation, be subsequently adding (195g, 3mol) zinc powder, control the temperature to be
16 DEG C, the glacial acetic acid of Deca (175ml, 3mol), drip and finish, sucking filtration after insulation reaction 5h, washs filter cake, merging filtrate is treated with methanol
With.
(3) synthesis of 9- anthraldehyde -1,1- diphenyl hydrazone: weigh the 9- anthracene first that (160g, 0.83mol) step (1) is obtained
In the four-hole bottle of 2.5l, 1, the 1- hydrazo-benzene filtrate that step (2) is obtained is added thereto aldehyde, and agitating heating maintains the temperature at
60 DEG C, after reaction 20h, filtered while hot, vacuum drying obtains yellow solid 260g, and yield is 90.0%.
Embodiment 4:
(1) preparation of 9- anthraldehyde: equipped with reflux condensing tube, thermometer, Dropping funnel, four mouthfuls of mechanical agitator burnings
Bottle in, add phosphorus oxychloride (210ml, 2.24mol) and anthracene (200g, 1.12mol), open agitator and heating, be warmed up to
100 DEG C, dmf (180ml, 2.52mol) is added in Dropping funnel, completion of dropping in 1h.Then after reaction 10h, cooling
Separate out crystal and obtain product 195g, fusing point is 104-105 DEG C.
(2) synthesis of 1,1- hydrazo-benzene: weigh the n- nitrosodiphenylamine that (198g, 1mol) refined and be added to 2.5l
Four-hole bottle in, and add the dehydrated alcohol of 450ml, magnetic agitation, be subsequently adding (195g, 3mol) zinc powder, control the temperature to be
20 DEG C, the glacial acetic acid of Deca (230ml, 4mol), drip and finish, sucking filtration after insulation reaction 5.5h, use washing with alcohol filter cake, merging filtrate
Stand-by.
(3) synthesis of 9- anthraldehyde -1,1- diphenyl hydrazone: weigh the 9- anthraldehyde that (155g, 0.8mol) step (1) is obtained
In the four-hole bottle of 2.5l, 1, the 1- hydrazo-benzene filtrate that step (2) is obtained is added thereto, and agitating heating maintains the temperature at 80
DEG C, after reaction 23h, filtered while hot, vacuum drying obtains yellow solid 265g, and yield is 92.0%.
Embodiment 5:
(1) preparation of 9- anthraldehyde: equipped with reflux condensing tube, thermometer, Dropping funnel, four mouthfuls of mechanical agitator burnings
Bottle in, add phosphorus oxychloride (236ml, 2.52mol) and anthracene (200g, 1.12mol), open agitator and heating, be warmed up to
110 DEG C, dmf (160ml, 2.24mol) is added in Dropping funnel, completion of dropping in 1h.Then after reaction 12h, cooling
Separate out crystal and obtain product 210g, fusing point is 104-105 DEG C.
(2) synthesis of 1,1- hydrazo-benzene: weigh the n- nitrosodiphenylamine that (198g, 1mol) refined and be added to 2.5l
Four-hole bottle in, and add the n-butyl alcohol of 450ml, magnetic agitation, be subsequently adding (260g, 4mol) zinc powder, control temperature to be 30
DEG C, the glacial acetic acid of Deca (230ml, 4mol), drip and finish, sucking filtration after insulation reaction 6h, washs filter cake, merging filtrate is treated with n-butyl alcohol
With.
(3) synthesis of 9- anthraldehyde -1,1- diphenyl hydrazone: weigh the 9- anthraldehyde that (144g, 0.7mol) step (1) is obtained
In the four-hole bottle of 2.5l, 1, the 1- hydrazo-benzene filtrate that step (2) is obtained is added thereto, and agitating heating maintains the temperature at 100
DEG C, after reaction 26h, filtered while hot, vacuum drying obtains yellow solid 240g, and yield is 91.0%.
Embodiment 6:
(1) preparation of 9- anthraldehyde: equipped with reflux condensing tube, thermometer, Dropping funnel, four mouthfuls of mechanical agitator burnings
Bottle in, add phosphorus oxychloride (262ml, 2.8mol) and anthracene (200g, 1.12mol), open agitator and heating, be warmed up to
120 DEG C, dmf (200ml, 2.8mol) is added in Dropping funnel, completion of dropping in 1h.Then after reaction 15h, cooling analysis
Go out crystal and obtain product 205g, fusing point is 104-105 DEG C.
(2) synthesis of 1,1- hydrazo-benzene: weigh the n- nitrosodiphenylamine that (198g, 1mol) refined and be added to 2.5l
Four-hole bottle in, and add the n-butyl alcohol of 450ml, magnetic agitation, be subsequently adding (325g, 5mol) zinc powder, control temperature to be 40
DEG C, the glacial acetic acid of Deca (287ml, 5mol), drip and finish, sucking filtration after insulation reaction 7h, washs filter cake, merging filtrate is treated with n-butyl alcohol
With.
(3) synthesis of 9- anthraldehyde -1,1- diphenyl hydrazone: weigh the 9- anthraldehyde that (134g, 0.6mol) step (1) is obtained
In the four-hole bottle of 2.5l, 1, the 1- hydrazo-benzene filtrate that step (2) is obtained is added thereto, and agitating heating maintains the temperature at 120
DEG C, after reaction 28h, filtered while hot, vacuum drying obtains yellow solid 230g, and yield is 95.0%.
Claims (10)
1. a kind of 9- anthraldehyde -1, the preparation method of 1- diphenyl hydrazone is it is characterised in that comprise the following steps:
(1) anthracene for 1:1:1-1:3:3 by mol ratio: phosphorus oxychloride: n, n- dimethylformamide adds in reaction vessel, 60-
120 DEG C of reaction 6-48h generate 9- anthraldehyde；
(2) the n- nitrosodiphenylamine for 1:1:1-1:7:7 by mol ratio: zinc: glacial acetic acid adds reaction vessel with alcohols solvent
In, 0-40 DEG C of reaction 1-9h generates 1,1- hydrazo-benzene；
(3) the 9- anthraldehyde for 1:1.2-1:2 by mol ratio: 1,1- hydrazo-benzene adds in reaction vessel, 30-120 DEG C of reaction, stir
Mix, cooling after reaction 12-48h has crystal to separate out, and after filtration, in benzene, recrystallization obtains product 9- anthraldehyde -1,1- diphenyl hydrazone.
2. method according to claim 1 it is characterised in that: step (1) anthracene, phosphorus oxychloride and n, n- dimethylformamide
Mol ratio be 1:2:2-1:2.5:2.5.
3. method according to claim 1 it is characterised in that: step (1) response time be 8-15h.
4. method according to claim 1 it is characterised in that: step (1) reaction temperature be 90-120 DEG C.
5. method according to claim 1 it is characterised in that: the rubbing of step (2) n- nitrosodiphenylamine, zinc and glacial acetic acid
That ratio is 1:3:3-1:5:5.
6. method according to claim 1 it is characterised in that: the alcohols solvent of step (2) is methanol, ethanol or positive fourth
Alcohol.
7. method according to claim 1 it is characterised in that: step (2) response time be 5-7h.
8. method according to claim 1 it is characterised in that: step (2) reaction temperature be 16-40 DEG C.
9. method according to claim 1 it is characterised in that: step (3) 9- anthraldehyde is rubbed with n- nitrosodiphenylamine
That ratio is 1:1.2-1:1.5.
10. method according to claim 1 it is characterised in that: step (3) reaction temperature be 60-120 DEG C；Response time
For 20-28h.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116218611A (en) * | 2021-12-06 | 2023-06-06 | 上海新阳半导体材料股份有限公司 | Polyimide cleaning fluid |
| CN116218610A (en) * | 2021-12-06 | 2023-06-06 | 上海新阳半导体材料股份有限公司 | Preparation method of polyimide cleaning liquid |
| CN116218612A (en) * | 2021-12-06 | 2023-06-06 | 上海新阳半导体材料股份有限公司 | Application of polyimide cleaning solution in cleaning semiconductor device |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4830944A (en) * | 1985-12-20 | 1989-05-16 | Canon Kabushiki Kaisha | Function separated photosensitive member having a diphenylamine derivative disazo charge generation material |
| JP2010002698A (en) * | 2008-06-20 | 2010-01-07 | Canon Inc | Electrophotographic photoreceptor, process cartridge and electrophotographic device |
| CN103232364A (en) * | 2004-06-29 | 2013-08-07 | 保土谷化学工业株式会社 | Process for producing hydrazone compound |
| CN105384648A (en) * | 2015-09-30 | 2016-03-09 | 常州市阳光药业有限公司 | Preparation method for 2,2'-di(methoxy)-4,4'-diaminophenyl |
-
2016
- 2016-08-16 CN CN201610682346.3A patent/CN106366017A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4830944A (en) * | 1985-12-20 | 1989-05-16 | Canon Kabushiki Kaisha | Function separated photosensitive member having a diphenylamine derivative disazo charge generation material |
| CN103232364A (en) * | 2004-06-29 | 2013-08-07 | 保土谷化学工业株式会社 | Process for producing hydrazone compound |
| JP2010002698A (en) * | 2008-06-20 | 2010-01-07 | Canon Inc | Electrophotographic photoreceptor, process cartridge and electrophotographic device |
| CN105384648A (en) * | 2015-09-30 | 2016-03-09 | 常州市阳光药业有限公司 | Preparation method for 2,2'-di(methoxy)-4,4'-diaminophenyl |
Non-Patent Citations (7)
| Title |
|---|
| RATHBONE, DANIEL 等: "Towards a polymeric binding mimic for cytochrome CYP2D6", 《BIOSENSORS AND BIOELECTRONICS》 * |
| 何莉莉 等: "芳香族腙类空穴传输材料的合成及其光电性能研究", 《应用化学》 * |
| 冯柏成 等: "对二甲胺基苯亚甲基-二苯腙的合成", 《青岛科技大学学报》 * |
| 李顺来 等: "短程有机电子给体-受体体系的合成", 《北京化工大学学报(自然科学版)》 * |
| 王海增 等: "9-蒽甲醛的合成", 《化工中间体》 * |
| 王海增: "9-恩甲醛的合成", 《化学试剂》 * |
| 王满力 等: "N,N-二苯基间三硝基苯肼自由基的合成", 《化学试剂》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116218611A (en) * | 2021-12-06 | 2023-06-06 | 上海新阳半导体材料股份有限公司 | Polyimide cleaning fluid |
| CN116218610A (en) * | 2021-12-06 | 2023-06-06 | 上海新阳半导体材料股份有限公司 | Preparation method of polyimide cleaning liquid |
| CN116218612A (en) * | 2021-12-06 | 2023-06-06 | 上海新阳半导体材料股份有限公司 | Application of polyimide cleaning solution in cleaning semiconductor device |
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Application publication date: 20170201 |