CN100417638C - Prepn process of nitro aromatic amine compound - Google Patents
Prepn process of nitro aromatic amine compound Download PDFInfo
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- CN100417638C CN100417638C CNB2005100149661A CN200510014966A CN100417638C CN 100417638 C CN100417638 C CN 100417638C CN B2005100149661 A CNB2005100149661 A CN B2005100149661A CN 200510014966 A CN200510014966 A CN 200510014966A CN 100417638 C CN100417638 C CN 100417638C
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- aromatic amine
- triphenylamine
- pentanoic
- reaction
- nitro aromatic
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- -1 nitro aromatic amine compound Chemical class 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 15
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims abstract description 11
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 6
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000004821 distillation Methods 0.000 claims abstract description 3
- 239000012535 impurity Substances 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims description 12
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 11
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 9
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 9
- 239000012312 sodium hydride Substances 0.000 claims description 9
- 238000001953 recrystallisation Methods 0.000 claims description 8
- AGHYMXKKEXDUTA-UHFFFAOYSA-N 4-methyl-n-phenylaniline Chemical compound C1=CC(C)=CC=C1NC1=CC=CC=C1 AGHYMXKKEXDUTA-UHFFFAOYSA-N 0.000 claims description 4
- TWPMMLHBHPYSMT-UHFFFAOYSA-N 3-methyl-n-phenylaniline Chemical compound CC1=CC=CC(NC=2C=CC=CC=2)=C1 TWPMMLHBHPYSMT-UHFFFAOYSA-N 0.000 claims description 3
- AGEQBLXZMIPKBM-UHFFFAOYSA-N 4-n,4-n-diphenylbenzene-1,2,3,4-tetramine Chemical compound NC1=C(N)C(N)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 AGEQBLXZMIPKBM-UHFFFAOYSA-N 0.000 claims description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 3
- MBPCKEZNJVJYTC-UHFFFAOYSA-N 4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 MBPCKEZNJVJYTC-UHFFFAOYSA-N 0.000 claims description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 6
- 150000004982 aromatic amines Chemical class 0.000 abstract description 5
- 230000005525 hole transport Effects 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract 6
- 239000003513 alkali Substances 0.000 abstract 1
- 125000005266 diarylamine group Chemical group 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000005181 nitrobenzenes Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 20
- 239000000706 filtrate Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000010792 warming Methods 0.000 description 6
- 229960000935 dehydrated alcohol Drugs 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XXYMSQQCBUKFHE-UHFFFAOYSA-N 4-nitro-n-phenylaniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1=CC=CC=C1 XXYMSQQCBUKFHE-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- AMAHTMJTDVOIFX-UHFFFAOYSA-N 4-methyl-n-(4-nitrophenyl)aniline Chemical compound C1=CC(C)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1 AMAHTMJTDVOIFX-UHFFFAOYSA-N 0.000 description 1
- XHVFCOOFJKCIAP-UHFFFAOYSA-N 4-n-(4-nitrophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1 XHVFCOOFJKCIAP-UHFFFAOYSA-N 0.000 description 1
- LMYRPNVAVVMMGC-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)C1=C(C=CC(=C1)N)C1=CC=C(N(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C1=C(C=CC(=C1)N)C1=CC=C(N(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 LMYRPNVAVVMMGC-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The present invention discloses a method for preparing nitro aromatic amine compounds, which belongs to the technology of preparing intermediate bodies of aromatic amine hole transport material. The preparing method comprises the steps that N, N-dimethylformamide is used as solvent, one of phenylamine, diphenylamine and triphenylamine is added in the solvent, strong alkali with the mole ratio of phenylamine to diphenylamine or triphenylamine of 1: 1 to 7: 1 is added, and p-fluoronitrobenzene or p-chloronitrobenzene with the mole ratio of phenylamine to diphenylamine or triphenylamine of 1: 1 to 5: 1 is added. The reaction temperature is kept within the range of 90 to 130 DEG C, the reaction is kept for 5 to 16 h, and then, hot filtration is utilized to eliminate impurities generated in the reaction process. DEF is eliminated through reduced pressure distillation, or the property that DEF dissolves in water and products don't dissolve in water is utilized to separate the products, and obtained primary products are recrystallized by using methanol, alcohol or acetonitrile to obtain relative nitro aromatic amine compounds. The present invention has the advantages of low prices of arylamine, diarylamine and halogenated nitrobenzene which are adopted as raw materials, simple post-treatment, high product yield and high purity and is suitable for industrialized production.
Description
Technical field
The invention relates to the preparation method of hole mobile material intermediate nitro aromatic amine compound, belong to the technology of preparing of hole mobile material intermediate.
Background technology
Arylamine hole transport material is the important component part of hole mobile material, because arylamine hole transport material has lower ionization potential and higher hole mobility, becomes the emphasis of people's research in recent years.But synthesize the good tri-arylamine group compound of hole transport performance, preparation as the aminated compounds for preparing one of product raw material is very important, there is the solvent that uses among the preparation method of nitro compound of document announcement that toluene, dimethylbenzene, oil of mirbane are arranged, but general long reaction time, the catalyzer costliness, and solvent toxicity is big.The invention provides that a kind of simple effectively the reaction times is short, the method that yield is high is for preparation arylamine hole transport material intermediate provides effective means.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of nitro aromatic amine compound, the nitro aromatic amine compound cost prepared with this method is low, and raw material is easy to use.
The present invention is realized by following technical proposals, a kind of preparation method of nitro aromatic amine, and its feature comprises following process:
In reaction vessel, with N, dinethylformamide (DMF) is a solvent, add aniline, pentanoic or triphenylamine a kind of, add again and aniline, pentanoic or triphenylamine mol ratio are 1: 1～7: 1 highly basic, add then and aniline, pentanoic or triphenylamine mol ratio are 1: 1～5: 1 p-fluoronitrobenzene or parachloronitrobenzene, keep 90～130 ℃ of temperature of reaction, reaction 5～16h, filtered while hot is removed the impurity that generates in the reaction process afterwards, underpressure distillation is removed DMF or is utilized DMF and water is miscible and the water-fast characteristic of product is separated out product, the head product that obtains is used methyl alcohol again, ethanol or acetonitrile recrystallization obtain corresponding nitryl arylamine compounds.
Above-mentioned aniline comprises aniline, para-totuidine, meta-aminotoluene, Ortho Toluidine;
Above-mentioned pentanoic comprises pentanoic, 4-methyldiphenylamine, 3 methyl diphenylamine, N, N-diphenylbenzidine, 4,4 '-dimethyl pentanoic or N, the N-diphenylbenzidine;
Above-mentioned triphenylamine comprise 4-triaminotriphenyl amine, 4-methyl-4 '-triaminotriphenyl amine, 3-methyl-4 '-triaminotriphenyl amine or 4,4 '-dimethyl-4 " triaminotriphenyl amine;
Above-mentioned highly basic comprises sodium hydride, sodium ethylate, potassium tert.-butoxide, sodium amide.
Embodiment
Synthesizing of example 1:4-nitrodiphenylamine
In being housed, the 250mL four-hole bottle of reflux condensing tube, thermometer and agitator adds 9.3g (0.1mol) aniline, 16.9g (0.12mol) p-fluoronitrobenzene, sodium hydride and the 150mLDMF of 4g (0.1mol) 60% stir and are warming up to 110 ℃, keep reaction 9h, reaction finishes the back filtered while hot, filtrate is diluted with a large amount of frozen water, filters the thick product dehydrated alcohol recrystallization that obtains, obtain product 18.7g, yield: 87.5%.
Example 2:4-methyl-4 '-nitrodiphenylamine synthetic
In being housed, the 250mL four-hole bottle of reflux condensing tube, thermometer and agitator adds 10.7g (0.1mol) para-totuidine, 16.9g (0.12mol) p-fluoronitrobenzene, sodium hydride and the 150mLDMF of 4g (0.1mol) 60% stir and are warming up to 110 ℃, keep reaction 9h, reaction finishes the back filtered while hot, filtrate is diluted with a large amount of frozen water, filters the thick product dehydrated alcohol recrystallization that obtains, obtain product 20.1g, yield: 88.1%.
Synthesizing of example 3:4-nitrotrianiline
In being housed, the 250mL four-hole bottle of reflux condensing tube, thermometer and agitator adds 16.9g (0.1mol) pentanoic, 16.9g (0.12mol) p-fluoronitrobenzene, sodium hydride and the 150mLDMF of 4g (0.1mol) 60% stir and are warming up to 110 ℃, keep reaction 9h, reaction finishes the back filtered while hot, filtrate is diluted with a large amount of frozen water, filters the thick product dehydrated alcohol recrystallization that obtains, obtain product 24.7g, yield: 85.2%.
Example 4:4-methyl-4 '-nitrotrianiline synthetic
In being housed, the 250mL four-hole bottle of reflux condensing tube, thermometer and agitator adds 18.3g (0.1mol) 4-methyldiphenylamine, 16.9g (0.12mol) p-fluoronitrobenzene, sodium hydride and the 150mLDMF of 4g (0.1mol) 60% stir and are warming up to 110 ℃, keep reaction 9h, reaction finishes the back filtered while hot, filtrate is diluted with a large amount of frozen water, filters the thick product dehydrated alcohol recrystallization that obtains, obtain product 26.2g, yield: 86.1%.
Example 5:N, N-two (4-nitrophenyl)-N ', N '-phenylbenzene-1,4-phenylenediamine synthetic
In being housed, the 250mL four-hole bottle of reflux condensing tube, thermometer and agitator adds 26g (0.1mol) 4-triaminotriphenyl amine, 33.8g (0.24mol) p-fluoronitrobenzene, sodium hydride and the 150mLDMF of 8g (0.2mol) 60% stir and are warming up to 110 ℃, keep reaction 15h, reaction finishes the back filtered while hot, filtrate is diluted with a large amount of frozen water, filters the thick product acetonitrile recrystallization that obtains, obtain product 23.8g, yield: 47.5%.
Example 6:N, N-two (4-nitrophenyl)-N ', N '-diphenylbenzidine synthetic
In being housed, the 250mL four-hole bottle of reflux condensing tube, thermometer and agitator adds 8.4g (0.025mol) N, the N-diphenylbenzidine, 8.5g (0.060mol) p-fluoronitrobenzene, sodium hydride and the 150mLDMF of 2g (0.050mol) 60%, stirring is warming up to 110 ℃, keep reaction 9h, reaction finishes the back filtered while hot, and filtrate is diluted with a large amount of frozen water, filter, the thick product acetonitrile recrystallization that obtains obtains product 9.5g, yield: 65.7%.
Synthesizing of example 7:4-nitrodiphenylamine
Sodium hydride is the 0.1mol sodium amide in the change example 1, and other condition is constant, obtains product 18.6g, yield: 87.1%.
Synthesizing of example 8:4-nitrotrianiline
The p-fluoronitrobenzene that changes in the example 3 is the parachloronitrobenzene of 0.12mol, and other condition is constant, obtains product 24.1g, yield: 83.1%.
Example 9:3-methyl-4 '-nitrotrianiline synthetic
The raw material 4-methyldiphenylamine that changes in the example 4 is a 3 methyl diphenylamine, and other condition is constant, obtains product 27.3g, yield: 86.9%.
Example 10:N, N-two (4-aminomethyl phenyl)-N ', N '-two (4-nitrophenyl)-1,4-phenylenediamine synthetic
Raw material 4-triaminotriphenyl amine in the change example 5 is 4,4 of 0.1mol '-dimethyl-4, and " triaminotriphenyl amine, other condition is constant, obtains product 25.4g, yield: 48.4%.
Claims (5)
1. the preparation method of a nitro aromatic amine, its feature comprises following process: in reaction vessel, with N, dinethylformamide is a solvent, add aniline, pentanoic or triphenylamine a kind of, add again and aniline, pentanoic or triphenylamine mol ratio are 1: 1～7: 1 highly basic, add then and aniline, pentanoic or triphenylamine mol ratio are 1: 1～5: 1 p-fluoronitrobenzene or parachloronitrobenzene, keep 90～130 ℃ of temperature of reaction, reaction 5～16h, filtered while hot is removed the impurity that generates in the reaction process afterwards, N is removed in underpressure distillation, dinethylformamide or utilize N, dinethylformamide and water is miscible and the water-fast characteristic of product is separated out product, the head product that obtains is used methyl alcohol again, ethanol or acetonitrile recrystallization obtain corresponding nitryl arylamine compounds.
2. by the preparation method of the described nitro aromatic amine of claim 1, it is characterized in that described aniline is aniline, para-totuidine, meta-aminotoluene or Ortho Toluidine.
3. by the preparation method of the described nitro aromatic amine of claim 1, it is characterized in that described pentanoic is pentanoic, 4-methyldiphenylamine, 3 methyl diphenylamine, N, N-diphenylbenzidine, 4,4 '-dimethyl pentanoic or N, the N-diphenylbenzidine.
4. by the preparation method of the described nitro aromatic amine of claim 1, it is characterized in that, described triphenylamine be 4-triaminotriphenyl amine, 4-methyl-4 '-triaminotriphenyl amine, 3-methyl-4 '-triaminotriphenyl amine or 4,4 '-dimethyl-4 " triaminotriphenyl amine.
5. by the preparation method of the described nitro aromatic amine of claim 1, it is characterized in that described highly basic is sodium hydride, sodium ethylate, potassium tert.-butoxide or sodium amide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100149661A CN100417638C (en) | 2005-09-02 | 2005-09-02 | Prepn process of nitro aromatic amine compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100149661A CN100417638C (en) | 2005-09-02 | 2005-09-02 | Prepn process of nitro aromatic amine compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1740141A CN1740141A (en) | 2006-03-01 |
| CN100417638C true CN100417638C (en) | 2008-09-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005100149661A Expired - Fee Related CN100417638C (en) | 2005-09-02 | 2005-09-02 | Prepn process of nitro aromatic amine compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100417638C (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1287116A (en) * | 1999-09-06 | 2001-03-14 | 拜尔公司 | Process for producing nitrodiphenyl amines |
| CN1517333A (en) * | 2003-01-07 | 2004-08-04 | Method for preparing nitrodiphenylamine |
-
2005
- 2005-09-02 CN CNB2005100149661A patent/CN100417638C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1287116A (en) * | 1999-09-06 | 2001-03-14 | 拜尔公司 | Process for producing nitrodiphenyl amines |
| CN1517333A (en) * | 2003-01-07 | 2004-08-04 | Method for preparing nitrodiphenylamine |
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| Publication number | Publication date |
|---|---|
| CN1740141A (en) | 2006-03-01 |
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