CN101230032A - Method for preparing 2,2-bi[3-(4-chlorinephthalimide)-4-hydroxyphenyl] propane - Google Patents
Method for preparing 2,2-bi[3-(4-chlorinephthalimide)-4-hydroxyphenyl] propane Download PDFInfo
- Publication number
- CN101230032A CN101230032A CNA2008100337931A CN200810033793A CN101230032A CN 101230032 A CN101230032 A CN 101230032A CN A2008100337931 A CNA2008100337931 A CN A2008100337931A CN 200810033793 A CN200810033793 A CN 200810033793A CN 101230032 A CN101230032 A CN 101230032A
- Authority
- CN
- China
- Prior art keywords
- propane
- hydroxy phenyl
- chlorine
- phthalimide group
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Landscapes
- Indole Compounds (AREA)
Abstract
The invention relates to a method for preparing 2, 2-bis [3-(4-chlorin phthalimide)-4-hydroxyphenyl] propane, which comprises the following steps: 2, 2-bis (3-amido-4- hydroxyphenyl) propane and 4-benzene anhydride monochloride with a molar ratio of 1.0:2.0 to 1.0:2.2 are mixed for reaction in strongly polar aprotic organic solvent in inertia atmosphere and room temperature. After becoming homogeneous solutions, they are added with azeotropic dehydrating agents for an azeotropic dehydrating reaction lasting for 2 to 12 hours. Then, the azeotropic dehydrating agents and part of strongly polar aprotic organic solvents are recycled, and the reaction solution is cooled to the room temperature. At last, water is added to separate the products out. The products are filtered, washed, and dried in vacuum. Characterized by simple operation, environmental protection, high yield rate and high purity of the product, and repeated recycling of solvent, the invention is suitable for industrialized production.
Description
Technical field
The invention belongs to the preparation field of organic compound, particularly relate to a kind of 2, the preparation method of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-.
Background technology
2, two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-are one of important raw and processed materials of preparation polyimide resin, polyesterimide resin, simultaneously, also are the good heat-proof modifier or the solidifying agent of Resins, epoxy.
Relevant 2, the preparation method of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-, not seeing as yet so far has patent or disclosed bibliographical information.
Summary of the invention
The purpose of this invention is to provide a kind of 2, the preparation method of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-, this method technology is simple, cost is low, environmentally friendly, yield, purity height are fit to suitability for industrialized production.
Of the present invention 2, two [3-(4-chlorine phthalimide group)-4-hydroxy phenyl] the propane chemical equations of 2-are as follows:
Of the present invention a kind of 2, the preparation method of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-comprises the steps:
(1) mol ratio be 1.0: 2.0～2.2 2, two (3-amino-4-hydroxy phenyl) propane and the 4-chloro-benzoic anhydrides of 2-, in strong polar non-proton organic solvent, stirring reaction under room temperature, after becoming homogeneous phase solution, add azeotropy dehydrant, heat temperature raising refluxes (85 ℃～180 ℃), azeotropic dehydration reaction 2～12 hours;
(2) reclaim the strong polar non-proton organic solvent of azeotropy dehydrant and part, the cooling reaction solution adds water to room temperature, separates out product, filtration, washing, and vacuum-drying obtains 2, two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-.
Described strong polar non-proton organic solvent is N, one or more mixtures in dinethylformamide (DMF), N,N-dimethylacetamide (DMAc), N-N-methyl-2-2-pyrrolidone N-(NMP), the dimethyl sulfoxide (DMSO) (DMSO).
Described 4-chloro-benzoic anhydride is 10 grams～30 grams with the weightmeasurement ratio of strong polar non-proton organic solvent: 20 milliliters～200 milliliters.
The described azeotropy dehydrant of step (1) is one or more mixtures in benzene,toluene,xylene, mono chloro benzene, the orthodichlorobenzene.
The volume ratio of described strong polar non-proton organic solvent of step (1) and azeotropy dehydrant is 1.0: 0.1～10.
The described cleaning solvent of step (2) is N, one or more in dinethylformamide (DMF), N,N-dimethylacetamide (DMAc) the N-N-methyl-2-2-pyrrolidone N-(NMP).
Beneficial effect of the present invention is as follows:
(1) the present invention is preparation 2, the commercial run of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-;
(2) environmentally friendly, the three wastes are few;
(3) simple to operate, reaction process is carried out under normal pressure, does not relate to also not producing corrosives, equipment there is not particular requirement, less investment can be finished preparation 2 in same reactor, the operating process of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-;
(4) product yield and purity are all very high;
(5) solvent is recyclable applies mechanically repeatedly, and this not only can reduce production costs, and has stopped environmental pollution effectively;
(6) production cost of products is cheap, helps it and further applies.
Description of drawings
Fig. 1 is 2, the molecular structure of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment only to be used to the present invention is described and be not used in and limit the scope of the invention.Should be understood that in addition those skilled in the art can make various changes or modifications the present invention after the content of having read the present invention's instruction, these equivalent form of values fall within the application's appended claims institute restricted portion equally.
Embodiment 1
With 0.05 mole 2, two (the 3-amino-4-hydroxy phenyl) propane (relative molecular weight 258.32) of 2-and 100 milliliters of N-N-methyl-2-2-pyrrolidone N-s (NMP) add in the reactor together, under the room temperature stirring and dissolving evenly after, add 0.1 mole of 4-chloro-benzoic anhydride (relative molecular weight 182.56), after stirring reaction is homogeneous phase, add 60 milliliters of dimethylbenzene, stir, heat temperature raising refluxes, after the azeotropic dehydration imidization 8 hours, reclaim the strong polar non-proton organic solvent N-N-methyl-2-2-pyrrolidone N-(NMP) of azeotropy dehydrant dimethylbenzene and part, close heating system, stir, naturally cool to room temperature, add water, separate out solid product, filter, with an amount of cold nmp solvent drip washing 2 times, vacuum-drying obtains 2, two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-, purity 99.1%, according to 2,2 of charging capacity of two (the 3-amino-4-hydroxy phenyl) propane of 2-and acquisition, the amount of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-, the yield that calculates product is 91.3%.
Embodiment 2
With 0.05 mole 2, two (the 3-amino-4-hydroxy phenyl) propane of 2-and 80 milliliters of N,N-dimethylacetamide (DMAc) add in the reactor together, under the room temperature stirring and dissolving evenly after, add 0.1 mole of 4-chloro-benzoic anhydride, after stirring reaction is homogeneous phase, add 80 milliliters of toluene, stir, heat temperature raising refluxes, after the azeotropic dehydration imidization 12 hours, reclaim the strong polar non-proton organic solvent N,N-dimethylacetamide (DMAc) of azeotropy dehydrant toluene and part, close heating system, stir, naturally cool to room temperature, add water, separate out solid product, filter, with an amount of cold N,N-dimethylacetamide (DMAc) eluent solvent 2 times, vacuum-drying, obtain 2, two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-, purity 99.3%, according to 2,2 of charging capacity of two (the 3-amino-4-hydroxy phenyl) propane of 2-and acquisition, the amount of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-, the yield that calculates product is 94.5%.
Embodiment 3
With 0.05 mole 2, two (the 3-amino-4-hydroxy phenyl) propane of 2-and 100 milliliters of N-N-methyl-2-2-pyrrolidone N-s (NMP) add in the reactor together, under the room temperature stirring and dissolving evenly after, add 0.1 mole of 4-chloro-benzoic anhydride, after stirring reaction is homogeneous phase, add 60 milliliters of dimethylbenzene, stir, heat temperature raising refluxes, after the azeotropic dehydration imidization 2 hours, reclaim the strong polar non-proton organic solvent N-N-methyl-2-2-pyrrolidone N-(NMP) of azeotropy dehydrant dimethylbenzene and part, close heating system, stir, naturally cool to room temperature, add water, separate out solid product, filter, with an amount of cold nmp solvent drip washing 2 times, vacuum-drying obtains 2, two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-, purity 98.2%, according to 2,2 of charging capacity of two (the 3-amino-4-hydroxy phenyl) propane of 2-and acquisition, the amount of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-, the yield that calculates product is 92.5%.
Embodiment 4
With 0.05 mole 2, two (the 3-amino-4-hydroxy phenyl) propane of 2-and 100 milliliters of N, dinethylformamide (DMF) adds in the reactor together, under the room temperature stirring and dissolving evenly after, add 0.11 mole of 4-chloro-benzoic anhydride, after stirring reaction is homogeneous phase, add 100 milliliters of toluene, stir, heat temperature raising refluxes, after the azeotropic dehydration imidization 12 hours, reclaim the strong polar non-proton organic solvent N of azeotropy dehydrant toluene and part, dinethylformamide (DMF), close heating system, stir, naturally cool to room temperature, add water, separate out solid product, filter, with an amount of cold N, dinethylformamide (DMF) eluent solvent 2 times, vacuum-drying, obtain 2, two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-, purity 98.7%, according to 2,2 of charging capacity of two (the 3-amino-4-hydroxy phenyl) propane of 2-and acquisition, the amount of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-, the yield that calculates product is 97.6%.
Embodiment 5
With 0.05 mole 2, two (the 3-amino-4-hydroxy phenyl) propane of 2-and 100 milliliters of N, dinethylformamide (DMF) adds in the reactor together, under the room temperature stirring and dissolving evenly after, add 0.105 mole of 4-chloro-benzoic anhydride, after stirring reaction is homogeneous phase, add 100 milliliters of toluene, stir, heat temperature raising refluxes, after the azeotropic dehydration imidization 10 hours, reclaim the strong polar non-proton organic solvent N of azeotropy dehydrant toluene and part, dinethylformamide (DMF), close heating system, stir, naturally cool to room temperature, add water, separate out solid product, filter, with an amount of cold N, dinethylformamide (DMF) eluent solvent 2 times, vacuum-drying, obtain 2, two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-, purity 99.0%, according to 2,2 of charging capacity of two (the 3-amino-4-hydroxy phenyl) propane of 2-and acquisition, the amount of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-, the yield that calculates product is 95.8%.
Claims (6)
1.2 the preparation method of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-comprises the steps:
(1) mol ratio be 1.0: 2.0～2.2 2, two (3-amino-4-hydroxy phenyl) propane and the 4-chloro-benzoic anhydrides of 2-, in strong polar non-proton organic solvent, stirring reaction under room temperature, after becoming homogeneous phase solution, add azeotropy dehydrant, 85 ℃～180 ℃ heat temperature raisings reflux, azeotropic dehydration reaction 2～～12 hours;
(2) reclaim azeotropy dehydrant and partly strong polar non-proton organic solvent, the cooling reaction solution adds water to room temperature, separates out product, filtration, washing, and vacuum-drying gets 2, two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-.
2. according to claim 12, the preparation method of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-, it is characterized in that: described strong polar non-proton organic solvent is selected from N, one or more mixtures among dinethylformamide DMF, N,N-dimethylacetamide DMAc, N-N-methyl-2-2-pyrrolidone N-NMP, the dimethyl sulfoxide (DMSO) DMSO.
3. according to claim 1 and 22, the preparation method of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-is characterized in that: described 4-chloro-benzoic anhydride is 10 grams～30 grams with the weightmeasurement ratio of strong polar non-proton organic solvent: 20 milliliters～200 milliliters.
4. according to claim 12, the preparation method of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-, it is characterized in that: the described azeotropy dehydrant of step (1) is selected from one or more mixtures in benzene,toluene,xylene, mono chloro benzene, the orthodichlorobenzene.
5. according to claim 12, the preparation method of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-, it is characterized in that: the volume ratio of described strong polar non-proton organic solvent of step (1) and azeotropy dehydrant is 1.0: 0.1～10.
6. according to claim 12, the preparation method of two [3-(4-chlorine the phthalimide group)-4-hydroxy phenyl] propane of 2-, it is characterized in that: the described cleaning solvent of step (2) is N, among dinethylformamide DMF, N,N-dimethylacetamide DMAc, the N-N-methyl-2-2-pyrrolidone N-NMP one or more.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008100337931A CN101230032A (en) | 2008-02-22 | 2008-02-22 | Method for preparing 2,2-bi[3-(4-chlorinephthalimide)-4-hydroxyphenyl] propane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008100337931A CN101230032A (en) | 2008-02-22 | 2008-02-22 | Method for preparing 2,2-bi[3-(4-chlorinephthalimide)-4-hydroxyphenyl] propane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101230032A true CN101230032A (en) | 2008-07-30 |
Family
ID=39896903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2008100337931A Pending CN101230032A (en) | 2008-02-22 | 2008-02-22 | Method for preparing 2,2-bi[3-(4-chlorinephthalimide)-4-hydroxyphenyl] propane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101230032A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110698644A (en) * | 2019-10-08 | 2020-01-17 | 东华大学 | Phthalimide glycidyl ester epoxy resin and preparation method thereof |
-
2008
- 2008-02-22 CN CNA2008100337931A patent/CN101230032A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110698644A (en) * | 2019-10-08 | 2020-01-17 | 东华大学 | Phthalimide glycidyl ester epoxy resin and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101307013B (en) | Aromatic diamine containing phthalonitrile side group, preparation method thereof and polyimide or polyamide prepared from aromatic diamine | |
| CN102604091B (en) | Polyimide containing benzimidazole unit and preparation method thereof | |
| CN100503569C (en) | Method for preparing 4,4'- bi (4 - carboxyl phthalimide group) 3,3'- dimethyl diphenylmothane | |
| CN105237767A (en) | Liquid-crystal polyamide imide and preparation method therefor | |
| CN104130177A (en) | Synthesis method of phthalonitrile and arylacetylene-terminated aromatic imide | |
| CN105504282B (en) | A kind of fluorenyl Cardo types polyimides diluent and its preparation method and application | |
| CN103058948B (en) | Benzoxazine monomer containing Schiff base structure, benzoxazine resin and preparation thereof | |
| CN101798463B (en) | High-performance polyimide film and preparation method thereof | |
| JP2014504652A (en) | Fusible polyimide molding compound and method for preparing the same | |
| CN104292230B (en) | Phthalimide-terminated monomer, preparation method and application thereof | |
| CN108395534A (en) | A kind of solubility height and the good bismaleimide performed polymer and its preparation method and application of temperature tolerance | |
| CN101235009A (en) | Method for preparing 2,2-di[3-(4-chlorophthalimido)-4-hydroxyphenyl]hexafluoropropane | |
| CN101921403A (en) | Synthesizing method of polyimide material | |
| CN109735917A (en) | A kind of ternary copolymerization polyimide spinning solution and preparation method | |
| CN108440754A (en) | One kind is containing tertiary butyl substitution m-Terphenyl structure polyimide film material and preparation method thereof | |
| CN101230031B (en) | Method for preparing 2,2-bi[3-(4-carboxylphthalimide)-4-hydroxyphenyl] hexafluoropropane | |
| CN101230032A (en) | Method for preparing 2,2-bi[3-(4-chlorinephthalimide)-4-hydroxyphenyl] propane | |
| CN110467725B (en) | Polynaphthaleneether ketone aromatic amide and preparation method and application thereof | |
| CN104761704A (en) | Modified epoxy resin and preparation method thereof, as well as modified epoxy resin composition and preparation method thereof | |
| CN104231269A (en) | Polyimide and preparation method thereof and polyimide molding powder | |
| CN101230030A (en) | Method for preparing 2,2-bi[3-(4-carboxylphthalimide)-4-hydroxyphenyl] propane | |
| CN101235010A (en) | Method for preparing 4,4'-di(4-carboxyphthalimido)-4''-hydroxytriphenylmethane | |
| CN104262233B (en) | Phthalimide-containing phthalonitrile monomer and its preparation method and use | |
| CN109928907A (en) | One kind having excellent machining property and reactive diluent resistant to high temperature and preparation method thereof | |
| CN101121689A (en) | Method for preparing 2,6-di[4-(4-carboxyphthalimido)phenoxy]cyanobenzene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Open date: 20080730 |