CN108456303B - Bio-based polyarylether resin containing furan ring structure and preparation method thereof - Google Patents

Bio-based polyarylether resin containing furan ring structure and preparation method thereof Download PDF

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CN108456303B
CN108456303B CN201810109871.5A CN201810109871A CN108456303B CN 108456303 B CN108456303 B CN 108456303B CN 201810109871 A CN201810109871 A CN 201810109871A CN 108456303 B CN108456303 B CN 108456303B
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furan ring
ring structure
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CN108456303A (en
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王锦艳
鲍锋
蹇锡高
刘程
柳承德
张守海
翁志焕
胡方圆
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Dalian University of Technology
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4006—(I) or (II) containing elements other than carbon, oxygen, hydrogen or halogen as leaving group (X)
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
    • C08G65/4031—(I) or (II) containing nitrogen
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4093—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group characterised by the process or apparatus used

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Abstract

The invention discloses a furan ring structure-containing bio-based polyarylether resin and a preparation method thereof, belonging to the technical field of polymer science. The furan ring structure-containing bio-based monomer furan-2, 5-di (4-fluorophenyl) ketone (BFBF) prepared by using bio-based derivative Furan Dicarboxylic Acid (FDAC) is subjected to nucleophilic substitution reaction with one or more of dihydric phenol monomer and dihalobenzophenone monomer to prepare the furan ring structure-containing bio-based homopolymerized or copolymerized polyaryletherketone resin. The biobased polyaryletherketone resin is introduced into the field of special engineering plastics, so that the variety of the polyaryletherketone resin is enriched, and the petroleum crisis is effectively coped with.

Description

Bio-based polyarylether resin containing furan ring structure and preparation method thereof
Technical Field
The invention belongs to the technical field of polymer science, relates to a novel polyarylether resin and a preparation method thereof, and particularly relates to a furan ring structure-containing bio-based polyarylether resin and a preparation method thereof.
Background
The polyaryletherketone resin is a novel high-temperature-resistant high-performance engineering plastic, has the advantages of high heat-resistant grade, excellent mechanical property, electrical property and radiation resistance, chemical resistance, fatigue resistance, impact resistance, creep resistance, wear resistance, flame retardance and the like, and is widely applied to many high and new technical fields of aviation, electronic information, energy and the like. However, conventional polyaryletherketone resins have been developed based on non-renewable petroleum resources. With the annual increase of the crude oil consumption in the world and the gradual decline of the petroleum reserves, the shortage of petroleum resources is bound to become the limitation of the further development of high-performance engineering plastic polyaryletherketone resin. Therefore, the research and development of the bio-based polyaryletherketone resin have very important time significance and will become the inevitable trend of future development.
Furan dicarboxylic acid (FDCA) is a biobased diacid [ LewkowskiJ. Synthesis, chemistry and applications of 5-Hydroxymethyl-furfuel and Its derivatives chemistry Chemform.2001, 34(2):37 ], similar in structure to terephthalic acid (PTA), prepared by catalytic oxidation of the biomass derivative 5-Hydroxymethylfurfural (HMF) [ Willem P.Dijkman, Daphene E.Groothuis, MarcoW.Fraje.AngewamInt Ed.2014,53(25): 6515-. With the increasing maturity of bio-based furandicarboxylic acid production technologies, numerous studies have been attempted using furandicarboxylic acid instead of terephthalic acid, such as polyesters containing furan ring structures (PEF, PPF, PBF) [ Knoop R JI, Vogelzang W, Haveren J.journal of Polymer Science Part A: Polymer chemistry.2013,51(19): 4191) 4199, epoxy resins [ Deng J, Liu X, Li C, Jiang Y, Zhu J.RSC adv.2015,5(21): 30 15939], polyimides, and the like. The research results show that the introduction of the furan ring structure does not reduce the performance of the material, and the furan ring structure is obviously improved in some aspects.
The subject group is dedicated to the research of petroleum-based polyaryletherketone resin, develops a series of polyaryletherketone resin with excellent performance, and is widely applied to the industries of aerospace, electronic and electrical, petroleum exploitation and the like. In view of the above, the invention starts from furandicarboxylic acid, prepares bio-based and dihalo-benzophenone monomers containing furan ring structures, creatively utilizes the bio-based dihalo-benzophenone monomer containing furan ring structures furan-2, 5-bis (4-fluorophenyl) ketone (BFBF), develops a class of bio-based homopolymerization (or copolymerization) polyaryletherketone resin containing furan ring structures, and aims to prepare polyaryletherketone resin by using bio-based monomers instead of petroleum-based monomers so as to deal with petroleum crisis and environmental problems. At present, no public report is found.
Disclosure of Invention
The invention relates to a furan ring structure-containing bio-based polyaryletherketone resin and a preparation method thereof. The preparation method comprises the step of carrying out nucleophilic polycondensation reaction on furan-2, 5-di (4-fluorophenyl) ketone (BFBF) as a biological group monomer containing a furan ring structure and one or more of a dihydric phenol monomer and dihalobenzophenone to prepare the polyaryletherketone resin containing the furan ring structure and the biological group homopolymerization (or copolymerization).
The technical scheme of the invention is as follows:
a furan ring structure-containing bio-based polyarylether resin has the following chemical structure:
Figure BDA0001568870810000021
wherein m is more than or equal to 1, and n is more than or equal to 0;
Figure BDA0001568870810000022
the structure of (1) is as follows:
Figure BDA0001568870810000023
Figure BDA0001568870810000024
the structure of (1) is as follows:
Figure BDA0001568870810000025
Figure BDA0001568870810000026
Figure BDA0001568870810000031
Figure BDA0001568870810000041
Figure BDA0001568870810000042
one or a combination of two or more of them; wherein, R, R1、R2、R3、R4、R5、R6、R7、R8The structure is as follows: H. f, Cl, Br, I, CN, NH2、Cr+1H2r+2、CrH2r+1、CrH2r+1COOH、OCrH2r+1、CF3、
Figure BDA0001568870810000043
One or more than two of the (a) and (b) are mixed, and r is more than or equal to 1; r, R1、R2、R3、R4、R5、R6、R7And R8The same or different;
Figure BDA0001568870810000044
the structure of (1) is as follows:
Figure BDA0001568870810000045
Figure BDA0001568870810000046
Figure BDA0001568870810000051
one or more than two of the components are mixed.
A preparation method of furan ring structure-containing bio-based polyarylether resin comprises the following polymerization reaction formula and steps:
Figure BDA0001568870810000052
wherein m is more than or equal to 1, n is more than or equal to 0, and X is F, Cl, Br or I;
Figure BDA0001568870810000053
the structure of (1) is as follows:
Figure BDA0001568870810000054
Figure BDA0001568870810000055
the structure of (1) is as follows:
Figure BDA0001568870810000056
Figure BDA0001568870810000057
Figure BDA0001568870810000061
Figure BDA0001568870810000071
Figure BDA0001568870810000072
one or a combination of two or more of them; wherein, R, R1、R2、R3、R4、R5、R6、R7、R8The structure is as follows: H. f, Cl, Br, I, CN, NH2、Cr+1H2r+2、CrH2r+1、CrH2r+1COOH、OCrH2r+1、CF3、
Figure BDA0001568870810000073
One or more than two of the (a) and (b) are mixed, and r is more than or equal to 1; r, R1、R2、R3、R4、R5、R6、R7And R8The same or different;
Figure BDA0001568870810000074
the structure of (1) is as follows:
Figure BDA0001568870810000075
Figure BDA0001568870810000076
Figure BDA0001568870810000077
one or more than two of the components are mixed;
the specific synthesis steps are as follows:
under the protection of inert gas, containing furan ring structure
Figure BDA0001568870810000078
Of a dihalogen monomer of
Figure BDA0001568870810000079
Structural dihydric phenol monomer, containing
Figure BDA00015688708100000710
Mixing a structural double-halogen monomer with alkali, adding a strong polar aprotic solvent and an azeotropic solvent, carrying out water treatment on a reaction system at the temperature of 110-150 ℃, removing the azeotropic solvent after reacting for 0.5-3 h, heating the reaction system to 160-200 ℃, reacting for 5-10 h, slowly pouring a viscous solution into a settling agent to obtain a fibrous substance, filtering, boiling for 10-24 h with boiling water, drying at the temperature of 100-150 ℃ for 10-24 h, and drying at the temperature of 90-150 ℃ under a vacuum condition to constant weight to obtain a crude polyaryletherketone resin product containing the furan ring structure bio-group homopolymerization or copolymerization; dissolving a crude polyaryletherketone resin product in a good solvent, wherein the mass ratio of the crude product to the good solvent is 1: 5-1: 35, filtering, settling filtrate in a settling agent, and sequentially filtering, drying by blowing and drying in vacuum to obtain the refined furan ring structure-containing bio-based polyaryletherketone resin;
wherein the molar ratio of the phenolic hydroxyl group to the halogen is 1: 0.9-1: 1.1, and the molar ratio of the alkali to the phenolic hydroxyl group is 1: 1.2-1: 2.2; the volume ratio of the azeotropic solvent to the mixed solvent is 1: 1-1: 3.
The structure containing furan ring
Figure BDA0001568870810000081
The reaction formula and the preparation method of the double-halogen monomer are as follows:
Figure BDA0001568870810000082
wherein, X has the structure: F. one of Cl, Br and I;
to be provided with
Figure BDA0001568870810000083
For example, the specific synthesis steps are as follows:
firstly, synthesizing a furan diformyl chloride intermediate, namely adding bio-based furan dicarboxylic acid and thionyl chloride into a reaction vessel with magnetic stirring according to the mass ratio of 0.2: 1-1: 1, and simultaneously adding a small amount of strong polar aprotic solvent DMF (1% of the volume of the thionyl chloride), wherein the reaction temperature is as follows: 60-100 ℃, reaction time: 2-6 hours. After the reaction is finished, cooling the system to room temperature, removing redundant thionyl chloride, and carrying out vacuum sublimation to obtain a white furan diformyl chloride FDCC crystal;
and secondly, under the protection of inert gas, taking the furan ring structure-containing bio-based intermediate FDCC and fluorobenzene as raw materials, taking Lewis acid as a catalyst, and reacting in a low-boiling-point organic solvent to prepare the target monomer. Wherein the mol ratio of FDCC to fluorobenzene is 1: 2-1: 5, the volume ratio of the low-boiling-point organic solvent to FDCC is 1: 3-1: 5, and the mol ratio of the Lewis acid catalyst to FDCC is 1: 2-1: 5; the reaction temperature is 25-100 ℃, and the reaction time is 10-24 h; after the reaction is finished, the mixture is settled in a settling agent, and the furan ring structure-containing bio-based dihalobenzophenone monomer BFBF is obtained after suction filtration, purification and drying.
Wherein, the inert gas is one of nitrogen, argon and helium.
The Lewis acid is one or the mixture of more than two of boron trichloride, boron tribromide, boron trifluoride and aluminum trichloride.
The low boiling point organic solvent is one or the mixture of more than two of chloroform, dichloromethane, dichloroethane and acetonitrile.
The alkali is one or more of potassium carbonate, cesium carbonate, sodium hydroxide and potassium hydroxide.
The strong polar aprotic solvent is one or a mixture of more than two of N, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone and sulfolane.
The azeotropic solvent is one or more of toluene, xylene and chlorobenzene.
The good solvent is one or a mixture of more than two of N, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, sulfolane and chloroform.
The settling agent is one or more of methanol, ethanol, isopropanol, acetone and water.
The invention has the beneficial effects that: the bio-based monomer furan dicarboxylic acid is used for designing and synthesizing a bio-based dihalobenzophenone monomer containing a furan ring structure, and then a series of excellent-performance bio-based homopolymerization (or copolymerization) polyaryletherketone resins containing the furan ring structure are prepared. The resin not only effectively deals with the petroleum crisis, but also can be regulated and controlled to obtain the target resin with high temperature resistance, dissolubility, easy processing and excellent mechanical property so as to meet the actual requirement.
Drawings
FIG. 1 is a 1H-NMR spectrum of a furan ring structure-containing bio-based polyaryletherketone resin PFBEK.
FIG. 2 is a 1H-NMR spectrum of a furan ring structure-containing bio-based polyaryletherketone resin PFBEK.
FIG. 3 is FT IR spectrum of furan ring structure-containing bio-based polyaryletherketone resins PFBEK and PFDEK.
Detailed Description
The following examples further illustrate the preparation method and properties of the furan ring structure-containing bio-based polyaryletherketone resin of the present invention, but do not represent the limitation of the present patent.
EXAMPLE 1 preparation of PFBEK
Under the protection of nitrogen atmosphere, a furan ring structure-containing bio-based monomer BFBF (10mmol,3.1227g), 9, 9-bis (4-hydroxyphenyl) fluorene BPF (10mmol,3.5042g) and anhydrous potassium carbonate K are added into a three-neck flask with mechanical stirring2CO3(14mmol,1.9023g) was dissolved in 4ml of sulfolaneReacting 1ml of N-methyl pyrrolidone and 10ml of toluene in a mixed solvent at 125-160 ℃ for 4h, evaporating the toluene in the mixed system, then heating to 195 ℃ for reaction for 10h, pouring the viscous solution into hot water to obtain a white fibrous polymer, boiling the fibrous polymer in boiling water for 8-12 h, and drying to constant weight to obtain a white furan ring structure-containing bio-based polyaryletherketone resin PFBEK crude product. Dissolving the crude product in chloroform according to a certain proportion, filtering, settling the filtered solution in absolute ethyl alcohol, and then sequentially filtering, drying by blowing and drying in vacuum to obtain the refined target product PFBEK with the yield of 99.9%. The nuclear magnetic and infrared characteristics of PFBEK are shown in the attached figures 1 and 2, and the heat resistance characteristics are shown in the table 1.
The structural formula is as follows:
Figure BDA0001568870810000101
EXAMPLE 2 preparation of polymer PFDEK
Under the protection of nitrogen atmosphere, a furan ring structure-containing bio-based monomer BFBF (10mmol,3.1227g), phthalazinone biphenyl DHPZ (10mmol,2.3824g) and anhydrous potassium carbonate K are added into a three-neck flask with mechanical stirring2CO3(14mmol,1.9023g) is dissolved in a mixed solvent of 3ml of sulfolane, 2ml of N, N-dimethylacetamide and 10ml of toluene, the mixture reacts for 4 hours at 125-160 ℃, the toluene in the mixed system is evaporated, then the temperature is raised to 195 ℃ for reaction for 10 hours, finally the viscous solution is poured into hot water to obtain a white fibrous polymer, the fibrous polymer is boiled by boiling water for 8-12 hours, and then the fibrous polymer is dried to constant weight to obtain a white crude product of the furan ring structure-containing bio-based polyaryletherketone resin PFDEK. And dissolving the crude product in chloroform according to a certain proportion, filtering, settling the filtered solution in absolute ethyl alcohol, and sequentially filtering, drying by blowing and drying in vacuum to obtain a refined target product PFDEK with the yield of 99.9%. The nuclear magnetic and infrared characterization of PFDEK is shown in fig. 3 and fig. 2, and the thermal performance test data is shown in table 1.
Figure BDA0001568870810000111
TABLE 1 thermal performance test of furan ring structure-containing bio-based polyaryletherketone resin PFBEK and PFDEK
And (6) obtaining the result.
Figure BDA0001568870810000112

Claims (10)

1. The furan ring structure-containing bio-based polyarylether resin is characterized by having the following chemical structure:
Figure FDA0002587880950000011
wherein m is more than or equal to 1;
Figure FDA0002587880950000012
the structure of (1) is as follows:
Figure FDA0002587880950000013
Figure FDA0002587880950000014
the structure of (1) is as follows:
Figure FDA0002587880950000015
Figure FDA0002587880950000016
Figure FDA0002587880950000017
one or a combination of two or more of them.
2. A preparation method of furan ring structure-containing bio-based polyarylether resin is characterized by comprising the following polymerization reaction formula and steps:
Figure FDA0002587880950000018
wherein m is more than or equal to 1, and X is any one of F, Cl, Br and I;
Figure FDA0002587880950000021
the structure of (1) is as follows:
Figure FDA0002587880950000022
Figure FDA0002587880950000023
the structure of (1) is as follows:
Figure FDA0002587880950000024
Figure FDA0002587880950000025
Figure FDA0002587880950000026
one or a combination of two or more of them;
the specific synthesis steps are as follows:
under the protection of inert gas, containing furan ring structure
Figure FDA0002587880950000027
Of a dihalogen monomer of
Figure FDA0002587880950000028
Mixing a structural dihydric phenol monomer with alkali, adding a strong polar aprotic solvent and an azeotropic solvent, carrying out water treatment on a reaction system at the temperature of 110-150 ℃, removing the azeotropic solvent after reacting for 0.5-3 h, heating the reaction system to 160-200 ℃, reacting for 5-10 h, slowly pouring a viscous solution into a settling agent to obtain a fibrous substanceFiltering, boiling in boiling water for 10-24 h, drying at 100-150 ℃ for 10-24 h, and drying at 90-150 ℃ under vacuum condition to constant weight to obtain a furan ring structure-containing bio-based copolymerized polyaryletherketone resin crude product; dissolving a crude polyaryletherketone resin product in a good solvent, wherein the mass ratio of the crude product to the good solvent is 1: 5-1: 35, filtering, settling filtrate in a settling agent, and sequentially filtering, drying by blowing and drying in vacuum to obtain the refined furan ring structure-containing bio-based polyaryletherketone resin;
wherein the molar ratio of the phenolic hydroxyl group to the halogen is 1: 0.9-1: 1.1, the molar ratio of the alkali to the phenolic hydroxyl group is 1: 1.2-1: 2.2, and the volume ratio of the azeotropic solvent to the mixed solvent is 1: 1-1: 3.
3. The method according to claim 2, wherein the furan ring-containing structure
Figure FDA0002587880950000031
The dihalogen monomer of (a) having the reaction formula:
Figure FDA0002587880950000032
wherein, X has the structure: F. cl, Br and I.
4. The production method according to claim 3,
Figure FDA0002587880950000033
the specific synthesis steps are as follows:
firstly, synthesizing a furan diformyl chloride intermediate: adding bio-based furandicarboxylic acid and thionyl chloride into a reaction container with magnetic stirring according to the mass ratio of 0.2: 1-1: 1, and simultaneously adding a strong polar aprotic solvent DMF which is 1% of the volume of the thionyl chloride, wherein the reaction temperature is as follows: 60-100 ℃, reaction time: 2-6 hours; after the reaction is finished, cooling the system to room temperature, removing redundant thionyl chloride, and carrying out vacuum sublimation to obtain a white furcellstructured bio-based intermediate furyldimethylchloride FDCC crystal;
under the protection of inert gas, taking a furan ring structure-containing bio-based intermediate FDCC and fluorobenzene as raw materials, taking Lewis acid as a catalyst, and reacting in a low-boiling-point organic solvent to prepare a target monomer; wherein the mol ratio of FDCC to fluorobenzene is 1: 2-1: 5, the volume ratio of the low-boiling-point organic solvent to FDCC is 1: 3-1: 5, and the mol ratio of the Lewis acid catalyst to FDCC is 1: 2-1: 5; the reaction temperature is 25-100 ℃, and the reaction time is 10-24 h; after the reaction is finished, the product is settled in a settling agent, and is subjected to suction filtration, purification and drying to obtain the product.
5. The method according to claim 4, wherein the base is one or more of potassium carbonate, cesium carbonate, sodium hydroxide, and potassium hydroxide.
6. The method according to claim 5, wherein the strongly polar aprotic solvent is one or a mixture of two or more of N, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide, N-methylpyrrolidone, and sulfolane.
7. The process according to claim 4 or 6, wherein the azeotropic solvent is one or a mixture of two or more of toluene, xylene and chlorobenzene.
8. The method according to claim 7, wherein the good solvent is one or a mixture of two or more of N, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide, N-methylpyrrolidone, sulfolane and chloroform.
9. The method according to claim 4, 6 or 8, wherein the settling agent is one or more of methanol, ethanol, isopropanol, acetone and water.
10. The method of claim 9, wherein the inert gas is one of nitrogen, argon, helium; the Lewis acid is one or the mixture of more than two of boron trichloride, boron tribromide, boron trifluoride and aluminum trichloride; the low boiling point organic solvent is one or the mixture of more than two of chloroform, dichloromethane, dichloroethane and acetonitrile.
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