CN106810628A - A kind of preparation method of polynitrobenzene ethene - Google Patents
A kind of preparation method of polynitrobenzene ethene Download PDFInfo
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- CN106810628A CN106810628A CN201611058893.0A CN201611058893A CN106810628A CN 106810628 A CN106810628 A CN 106810628A CN 201611058893 A CN201611058893 A CN 201611058893A CN 106810628 A CN106810628 A CN 106810628A
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- polynitrobenzene
- ethene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F112/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F112/02—Monomers containing only one unsaturated aliphatic radical
- C08F112/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F112/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to organic polymer field, and in particular to a kind of polynitrobenzene ethene.The one-step synthesis of polynitrobenzene ethene is carried out using fuming nitric aicd, concentrated sulfuric acid consumption increases, the relative molecular mass increase of polynitrobenzene ethene, yield are improved.This preparation method has the advantages that the reaction time is short, nitro Drug delivery rate is high, and method is simple, with low cost, can be used for industrial production.
Description
Technical field
The present invention relates to organic polymer field, and in particular to a kind of polynitrobenzene ethene.
Background technology
Polystyrene（PS）Phenyl ring be prone to reaction kinetic（Such as nitrification, sulfonation）, the hydrogen atom on phenyl ring is by nitro
Substitution is polynitrobenzene ethene, and reduction nitro then generates polyamine group styrene.This kind of functional polymer is in self assembly, biological doctor
Have broad application prospects with fields such as macromolecule, water process, ion exchange resin, intercalating agent, immobilized catalyst and dyestuffs.
Bachman etc. is earliest by PS by nitrification, reduction, diazotising and coupling four-step reaction（Abbreviation NRDC reaction schemes）It is prepared for idol
Nitrogen polymer.The synthesis of such polynitrobenzene ethene is using crosslinking PS matrixes, and reaction interface is small, and Nitrification rate is not high and final product
It is insoluble, reaction kinetic yield is have impact on, also limit their applications in terms of solubility.
Open crystalline substance etc. and improve NRDC reaction schemes, non-crosslinked PS is nitrified as solvent with meta-nitrotoluene higher
Nitrification rate, but meta-nitrotoluene price is high have impact on this research application industrially.Kim etc. nitrifies PS, prepared by reduction
Poly- aminostyryl, as the basic material of functional polymer film.It can be seen that polynitrobenzene ethene has turned into various functions high score
The intermediate materials of son, the quality of its quality directly affects the performance of functional high molecule material.
The content of the invention
The technical problem to be solved in the present invention is to provide a kind of preparation method of polynitrobenzene ethene.
In order to achieve the above object, the present invention is adopted the following technical scheme that：
To the acid of 20 ~ 40 weight portions and 30 ~ 40 parts by weight solvent are added in a mixing bowl by dried process, stirring is then turned on
1h, is cooled to 0 DEG C, is slowly dropped into 100 quantitative weight parts of styrene monomer, stirs 3h, is added dropwise to absolute ethyl alcohol and terminates anti-
Should, product is filtrated to get the product of clear crystal.Product is washed with deionized water, after be dried to constant weight.Its chemistry is anti-
Answer formula as follows：
Further, described acid is the mixing of the mixture, fuming nitric aicd and concentrated hydrochloric acid of fuming nitric aicd, fuming nitric aicd and the concentrated sulfuric acid
One kind in thing；The preferably mixture of fuming nitric aicd and the concentrated sulfuric acid.
Further, described solvent is the one kind in normal heptane, dichloromethane, monochloro methane；Preferably dichloromethane.
Beneficial effect
Compared with traditional NRDC reaction schemes, the preparation method has the preparation method of polynitrobenzene ethene provided by the present invention
Have the advantages that the reaction time is short, nitro Drug delivery rate is high, and method is simple, with low cost, can be used for industrial production.
Implementation method
Below by specific embodiment, technical scheme is further illustrated, but the present invention is not limited
In these examples.
Embodiment 1：
To the mixture that 20 weight portion fuming nitric aicds and the concentrated sulfuric acid are added in a mixing bowl by dried process（Ratio is 1:1）,
40 weight parts Methylene chlorides, are then turned on stirring 1h, are cooled to 0 DEG C, are slowly dropped into 100 quantitative weight parts of styrene monomer,
Stirring 3h, is added dropwise to absolute ethyl alcohol terminating reaction, product is filtrated to get the product of clear crystal.By product spend from
Constant weight is dried to after son washing.
It is 87%, nitro Drug delivery rate 96% to be calculated yield using weighing method.
Embodiment 2：
To the mixture that 30 weight portion fuming nitric aicds and the concentrated sulfuric acid are added in a mixing bowl by dried process（Ratio is 1:2）,
30 weight parts Methylene chlorides, are then turned on stirring 1h, are cooled to 0 DEG C, are slowly dropped into 100 quantitative weight parts of styrene monomer,
Stirring 3h, is added dropwise to absolute ethyl alcohol terminating reaction, product is filtrated to get the product of clear crystal.By product spend from
Constant weight is dried to after son washing.
It is 92%, nitro Drug delivery rate 98% to be calculated yield using weighing method.
Embodiment 3：
To the mixture that 30 weight portion fuming nitric aicds and the concentrated sulfuric acid are added in a mixing bowl by dried process（Ratio is 1:3）,
30 weight parts Methylene chlorides, are then turned on stirring 1h, are cooled to 0 DEG C, are slowly dropped into 100 quantitative weight parts of styrene monomer,
Stirring 3h, is added dropwise to absolute ethyl alcohol terminating reaction, product is filtrated to get the product of clear crystal.By product spend from
Constant weight is dried to after son washing.
It is 96%, nitro Drug delivery rate 98% to be calculated yield using weighing method.
Embodiment 4：
To the mixture that 30 weight portion fuming nitric aicds and the concentrated sulfuric acid are added in a mixing bowl by dried process（Ratio is 1:3）,
The mixture of 30 weight parts Methylene chlorides and normal heptane（Ratio is 1:1）, it is then turned on stirring 1h, 0 DEG C is cooled to, it is slowly dropped into
100 quantitative weight parts of styrene monomer, stir 3h, are added dropwise to absolute ethyl alcohol terminating reaction, product is filtrated to get nothing
The product of color crystal.Constant weight is dried to after product is washed with deionized water.
It is 88%, nitro Drug delivery rate 99% to be calculated yield using weighing method.
Finally it should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention rather than the present invention is protected
The limitation of scope, although being elaborated to the present invention with reference to preferred embodiment, one of ordinary skill in the art should manage
Solution, can modify or equivalent, without deviating from the essence and model of technical solution of the present invention to technical scheme
Enclose.
Claims (5)
1. a kind of preparation method of polynitrobenzene ethene, it is characterised in that including：
To the acid of 20 ~ 40 weight portions and 30 ~ 40 parts by weight solvent are added in a mixing bowl by dried process, stirring is then turned on
1h, is cooled to 0 DEG C, is slowly dropped into 100 quantitative weight parts of styrene monomer, stirs 3h, is added dropwise to absolute ethyl alcohol and terminates anti-
Should, product is filtrated to get the product of clear crystal；
Product is washed with deionized water, after be dried to constant weight；
Its chemical equation is as follows：
。
2. the preparation method of a kind of polynitrobenzene ethene according to claim 1, it is characterised in that described acid is smoke
One kind in the mixture of the mixture, fuming nitric aicd and concentrated hydrochloric acid of nitric acid, fuming nitric aicd and the concentrated sulfuric acid.
3. the preparation method of a kind of polynitrobenzene ethene according to claim 2, it is characterised in that described acid is smoke
The mixture of nitric acid and the concentrated sulfuric acid.
4. the preparation method of a kind of polynitrobenzene ethene according to claim 1, it is characterised in that described solvent is for just
One kind in heptane, dichloromethane, monochloro methane.
5. the preparation method of a kind of polynitrobenzene ethene according to claim 4, it is characterised in that described solvent is two
Chloromethanes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611058893.0A CN106810628A (en) | 2016-11-28 | 2016-11-28 | A kind of preparation method of polynitrobenzene ethene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611058893.0A CN106810628A (en) | 2016-11-28 | 2016-11-28 | A kind of preparation method of polynitrobenzene ethene |
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| CN106810628A true CN106810628A (en) | 2017-06-09 |
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| CN201611058893.0A Pending CN106810628A (en) | 2016-11-28 | 2016-11-28 | A kind of preparation method of polynitrobenzene ethene |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103497082A (en) * | 2013-09-24 | 2014-01-08 | 台州学院 | Method for preparing beta-nitrostyrolene and derivatives thereof |
| CN104418753A (en) * | 2013-08-21 | 2015-03-18 | 南京理工大学 | Method for green-catalytically synthesizing nitrobenzaldehyde |
| CN104974047A (en) * | 2014-04-03 | 2015-10-14 | 长春工业大学 | Method for preparing aminostyrene through catalytic hydrogenation of nitrostyrene |
| CN105152935A (en) * | 2015-09-06 | 2015-12-16 | 安徽理工大学 | Method for preparing beta-nitrostyrolene compound |
-
2016
- 2016-11-28 CN CN201611058893.0A patent/CN106810628A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104418753A (en) * | 2013-08-21 | 2015-03-18 | 南京理工大学 | Method for green-catalytically synthesizing nitrobenzaldehyde |
| CN103497082A (en) * | 2013-09-24 | 2014-01-08 | 台州学院 | Method for preparing beta-nitrostyrolene and derivatives thereof |
| CN104974047A (en) * | 2014-04-03 | 2015-10-14 | 长春工业大学 | Method for preparing aminostyrene through catalytic hydrogenation of nitrostyrene |
| CN105152935A (en) * | 2015-09-06 | 2015-12-16 | 安徽理工大学 | Method for preparing beta-nitrostyrolene compound |
Non-Patent Citations (1)
| Title |
|---|
| 朱瑞: "聚硝基苯乙烯的一步合成I.聚合工艺、溶剂极性、浓硫酸用量的影响", 《合成树脂及塑料》 * |
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Application publication date: 20170609 |