CN102924297A - Synthesis of triphenylamine compound with high fluorescence - Google Patents
Synthesis of triphenylamine compound with high fluorescence Download PDFInfo
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- CN102924297A CN102924297A CN2012104718500A CN201210471850A CN102924297A CN 102924297 A CN102924297 A CN 102924297A CN 2012104718500 A CN2012104718500 A CN 2012104718500A CN 201210471850 A CN201210471850 A CN 201210471850A CN 102924297 A CN102924297 A CN 102924297A
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- benzene
- methyl
- phenyl
- ethylphenyl
- amino
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a method for synthesizing 1,4-bis (4-(N-2-methyl-6-ethyl phenyl)-N- phenyl) aminobenzene ethenyl)-benzene through serial reaction of substitution, condensation and the like, by taking substituted aniline as raw material. The synthesis general formula is as follows: R=Cl, and the overall yield of Br in three steps is more than 30 percent, so that triphenylamine compound is possible to be applicable to industrial production. The invention discloses a preparation method of the triphenylamine compound.
Description
Technical field
The present invention relates to Isosorbide-5-Nitrae-two 4-[N-2-methyl-6-ethylphenyl)-the N-phenyl] the amino-benzene vinyl-preparation method of benzene.
Technical background
At present, do not have the concrete document about this compou nd synthesis, and this compound is the main component of green ink on the color printer.
Summary of the invention
The invention describes Isosorbide-5-Nitrae-two 4-[N-2-methyl-6-ethylphenyl)-the N-phenyl] the amino-benzene vinyl-preparation method of benzene, the three-step reaction productive rate can reach 31%.
Embodiment
Further describe the present invention by following examples, but should notice that scope of the present invention is not subjected to any restriction of these embodiment.
Synthesizing of (2-methyl-6-ethylphenyl)-triphenylamine (1)
Embodiment 1:Under the nitrogen protection, 2-methyl-6-ethylaniline, chlorobenzene, palladium (II); phosphorus part and sodium tert-butoxide refluxed 5 hours at o-Xylol, and active earths is processed, and filtered, and be concentrated; add methyl alcohol, filter to get the dark white solid, get product through recrystallization purifying, yield 62%.
Embodiment 2:Under the nitrogen protection, 2-methyl-6-ethylaniline, bromobenzene, palladium (II); phosphorus part and sodium tert-butoxide refluxed 5 hours at o-Xylol, and active earths is processed, and filtered, and be concentrated; add methyl alcohol, filter to get the dark white solid, get product through recrystallization purifying, yield 71%.
Synthesizing of (2-methyl-6-ethylphenyl)-N-phenyl-4-aminobenzaldehyde (2)
Compound (1) is dissolved in dimethyl formamide, and oxygen phosphorus is dissolved among the DMF, slowly joins mentioned solution, 80 degree reaction 5h, hydrolysed filtrate gets solid, and washing is dissolved into toluene, washing, anhydrous sodium sulfate drying, active earths is processed, the concentrated rear methyl alcohol that adds, product (72.6%) is filtered to get in cooling.
Synthesizing of compound (3)
Benzyl dichloride and triethyl-phosphite were refluxed 4 hours, and the cooling of reaction solution mixture adds normal hexane, is cooled to about 10 degree, obtains white solid, yield 86.1%.
, 4-two 4-[N-2-methyl-6-ethylphenyl)-the N-phenyl] the amino-benzene vinyl-benzene (4) synthetic
Embodiment 1:Under the nitrogen protection, add methanol solution of sodium methylate, compound (3) and 40 milliliters of tetrahydrofuran (THF)s; stirred 30 minutes in the ice bath, compound (2) is dissolved in tetrahydrofuran (THF) and is added drop-wise in the reaction mixture, stirring at room 15 hours; then be hydrolyzed, and extract evaporation concentration with toluene; residue is dissolved in the toluene; use activated carbon treatment, the concentrated rear methyl alcohol that adds, cooling; filter to get product, yield 61.7%.
Embodiment 2:Under the nitrogen protection, add methanol solution of sodium methylate, compound (3) and DMF; stirred 30 minutes in the ice bath, compound (2) is dissolved in DMF and is added drop-wise to reaction mixture, stirring at room 15 hours; then be hydrolyzed, and extract evaporation concentration with toluene; residue is dissolved in the toluene; use activated carbon treatment, the concentrated rear methyl alcohol that adds, cooling; filter to get product, yield 61%.
Claims (3)
1. one kind take substituted aniline as raw material, through replacement and the serial reactions such as condensation synthesize Isosorbide-5-Nitrae-two 4-[N-2-methyl-6-ethylphenyl)-the N-phenyl] the amino-benzene vinyl-method of benzene, its synthetic general formula is as follows:
R?=?Cl,?Br。
2. one kind claimed in claim 11; 4-two 4-[N-2-methyl-6-ethylphenyl)-the N-phenyl] the amino-benzene vinyl-preparation method of benzene; it is characterized in that: substituted aniline is raw material; o-Xylol is solvent; obtain triphenylamine by palladium catalysis and halobenzene reaction; continue formylation, the Isosorbide-5-Nitrae of final preparation-two 4-[N-2-methyl-6-ethylphenyl)-the N-phenyl] the amino-benzene vinyl }-benzene.
As claim 1 or 2 each described Isosorbide-5-Nitraes-two 4-[N-2-methyl-6-ethylphenyl)-the N-phenyl] the amino-benzene vinyl-application of preparation method in industrial production of benzene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012104718500A CN102924297A (en) | 2012-11-21 | 2012-11-21 | Synthesis of triphenylamine compound with high fluorescence |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012104718500A CN102924297A (en) | 2012-11-21 | 2012-11-21 | Synthesis of triphenylamine compound with high fluorescence |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102924297A true CN102924297A (en) | 2013-02-13 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2012104718500A Pending CN102924297A (en) | 2012-11-21 | 2012-11-21 | Synthesis of triphenylamine compound with high fluorescence |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6022998A (en) * | 1997-07-24 | 2000-02-08 | Mita Industrial Co., Ltd. | Stilbene derivative and method for producing the same |
| WO2002079691A1 (en) * | 2001-03-30 | 2002-10-10 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Materials, methods, and uses for photochemical generation of acids and/or radical species |
| CN1605945A (en) * | 2003-09-30 | 2005-04-13 | 京瓷美达株式会社 | Stilbene inducer, process for producing the same, and electrophotographic photoconductor |
| JP2007045758A (en) * | 2005-08-10 | 2007-02-22 | Kyocera Mita Corp | Method of purifying diamine compound |
| CN102516088A (en) * | 2011-11-28 | 2012-06-27 | 徐州宇家化工科技有限公司 | Combination of triphenylamine compound with strong fluorescence |
-
2012
- 2012-11-21 CN CN2012104718500A patent/CN102924297A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6022998A (en) * | 1997-07-24 | 2000-02-08 | Mita Industrial Co., Ltd. | Stilbene derivative and method for producing the same |
| WO2002079691A1 (en) * | 2001-03-30 | 2002-10-10 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Materials, methods, and uses for photochemical generation of acids and/or radical species |
| CN1605945A (en) * | 2003-09-30 | 2005-04-13 | 京瓷美达株式会社 | Stilbene inducer, process for producing the same, and electrophotographic photoconductor |
| JP2007045758A (en) * | 2005-08-10 | 2007-02-22 | Kyocera Mita Corp | Method of purifying diamine compound |
| CN102516088A (en) * | 2011-11-28 | 2012-06-27 | 徐州宇家化工科技有限公司 | Combination of triphenylamine compound with strong fluorescence |
Non-Patent Citations (3)
| Title |
|---|
| HAIQIAO WANG 等: "Synthesis and characterization of a partial-conjugated hyperbranched poly(p-phenylene vinylene) (HPPV)", 《SYNTHETIC METALS》 * |
| JOEL M. KAUFFMAN 等: "Diarylamino Groups as Photostable Auxofluors in 2-Benzoxazolylfluorene, 2,5-Diphenyloxazoles, 1,3,5-Hexatrienes, 1,4-Distyrylbenzenes, and 2,7-Distyrylfluorenes", 《J.ORG.CHEM.》 * |
| 孙萍萍: "二苯乙烯类荧光增白剂1,4-二(邻氰基苯乙烯基)苯的合成及晶体结构与光物理性质", 《青岛科技大学学报（自然科学版）》 * |
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Application publication date: 20130213 |