CN113773418A - Polystyrene selenizing method using diselenide as selenium source - Google Patents
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- XIMIGUBYDJDCKI-UHFFFAOYSA-N diselenium Chemical compound [Se]=[Se] XIMIGUBYDJDCKI-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 239000004793 Polystyrene Substances 0.000 title claims abstract description 38
- 229920002223 polystyrene Polymers 0.000 title claims abstract description 38
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 229910052711 selenium Inorganic materials 0.000 title claims abstract description 34
- 239000011669 selenium Substances 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- PCMOZDDGXKIOLL-UHFFFAOYSA-K yttrium chloride Chemical compound [Cl-].[Cl-].[Cl-].[Y+3] PCMOZDDGXKIOLL-UHFFFAOYSA-K 0.000 claims abstract description 19
- 239000011259 mixed solution Substances 0.000 claims abstract description 15
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 9
- YWWZCHLUQSHMCL-UHFFFAOYSA-N diphenyl diselenide Chemical compound C=1C=CC=CC=1[Se][Se]C1=CC=CC=C1 YWWZCHLUQSHMCL-UHFFFAOYSA-N 0.000 claims description 17
- 238000002791 soaking Methods 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 5
- ARWXFTYBPFRIBM-UHFFFAOYSA-N 1-(butyldiselanyl)butane Chemical compound CCCC[Se][Se]CCCC ARWXFTYBPFRIBM-UHFFFAOYSA-N 0.000 claims description 4
- NRZFMEPRSSEGOP-UHFFFAOYSA-N 1-[[3,5-bis(trifluoromethyl)phenyl]diselanyl]-3,5-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC([Se][Se]C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 NRZFMEPRSSEGOP-UHFFFAOYSA-N 0.000 claims description 4
- KJCNOACMRYZZFR-UHFFFAOYSA-N 1-methyl-4-[(4-methylphenyl)diselanyl]benzene Chemical compound C1=CC(C)=CC=C1[Se][Se]C1=CC=C(C)C=C1 KJCNOACMRYZZFR-UHFFFAOYSA-N 0.000 claims description 4
- CBQLVACGEMGVMI-UHFFFAOYSA-N 2-(pyridin-2-yldiselanyl)pyridine Chemical compound C=1C=CC=NC=1[Se][Se]C1=CC=CC=N1 CBQLVACGEMGVMI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 abstract description 27
- 238000006555 catalytic reaction Methods 0.000 abstract description 3
- 230000003115 biocidal effect Effects 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 description 17
- 230000008961 swelling Effects 0.000 description 7
- 150000003959 diselenides Chemical group 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 238000005906 dihydroxylation reaction Methods 0.000 description 2
- VLXBWPOEOIIREY-UHFFFAOYSA-N dimethyl diselenide Chemical compound C[Se][Se]C VLXBWPOEOIIREY-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000007336 electrophilic substitution reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 150000003346 selenoethers Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 1
- HOFDWPHQRUGAEI-UHFFFAOYSA-N acetonitrile;cyclohexene Chemical compound CC#N.C1CCC=CC1 HOFDWPHQRUGAEI-UHFFFAOYSA-N 0.000 description 1
- HFNDSOBLEIOGHW-UHFFFAOYSA-N acetonitrile;hydrogen peroxide Chemical compound OO.CC#N HFNDSOBLEIOGHW-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 229910052798 chalcogen Inorganic materials 0.000 description 1
- 150000001787 chalcogens Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 238000010506 ionic fission reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002957 persistent organic pollutant Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- QYHFIVBSNOWOCQ-UHFFFAOYSA-N selenic acid Chemical compound O[Se](O)(=O)=O QYHFIVBSNOWOCQ-UHFFFAOYSA-N 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- -1 yttrium trichloride Selenium Chemical compound 0.000 description 1
Classifications
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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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling
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- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for selenizing polystyrene by taking diselenide as a selenium source, which belongs to the technical field of material chemical industry, and is characterized in that polystyrene is soaked in cyclohexane for 12-36 hours, then filtered and dried, and then placed in a mixed solution composed of diselenide, yttrium trichloride and dichloromethane for selenizing reaction for 24-48 hours, so that selenized polystyrene is obtained. The method uses diselenide which is easy to obtain, stable and variable in substituent as a selenium source, the reaction condition is mild, and the prepared material has potential application value in the fields of catalysis, antibiosis, environmental management and the like.
Description
Technical Field
The invention belongs to the technical field of material chemical industry, and particularly relates to a selenization method of polystyrene.
Background
Selenium is a chalcogen with unique properties. It is capable of binding oxygen, but the seleno-oxygen bond is not strong. Low-valent selenium is easily oxidized, while high-valent selenium is an oxidant. Thus, selenium-containing compounds and materials can act as an "oxygen carrier" to carry elemental oxygen to the reactants to catalyze oxidation reactions, both in synthesis and in the oxidative degradation of organic pollutants (chi. chem. lett. 2020, 31, 1078). In addition, the oxygen-carrying capacity of selenium is also beneficial to destroying cell membranes and increasing the active oxygen content in cells, thereby achieving the bactericidal effect (Chin. chem. Lett. 2020, 31, 1887). Therefore, the synthesis of selenium-containing compounds and materials is an important application subject.
Polystyrene is a common and readily available high polymer material. The polystyrene is used as a carrier platform to develop related selenium-immobilized materials, and the method has good practical significance. For example, we have previously successfully developed polystyrene-supported selenic acid and applied it to cyclohexene dihydroxylation reactions (j. mater. chem. a, 2016, 4, 10828). However, the existing method has various steps, needs to go through multiple steps such as lithiation, selenium insertion, oxidation and the like, and uses flammable, explosive, toxic and malodorous reagents such as butyl lithium, dimethyl diselenide, hydrogen peroxide and the like. These disadvantages limit the large-scale application of this material. Therefore, the development of a method for selenizing polystyrene under mild conditions is very necessary from the application point of view.
Disclosure of Invention
The invention aims to provide a method for selenizing polystyrene by using diselenide as a selenium source.
The technical scheme provided by the invention is as follows: soaking polystyrene in cyclohexane for 12-36 hours, filtering, drying, and placing the polystyrene in a mixed solution composed of diselenide, yttrium trichloride and dichloromethane for selenylation reaction for 24-48 hours to obtain the selenylated polystyrene.
The invention only needs diselenide which is easy to obtain, stable and changeable in substituent group as a selenium source, and can realize the selenization of polystyrene through unique selenium-selenium bond heterolytic cleavage and benzene ring electrophilic substitution reaction under the catalysis of a small amount of yttrium trichloride. The invention has the advantages of easily obtained raw materials, mild reaction conditions and simple method, and the prepared material has potential application value in the fields of catalysis, antibiosis, environmental management and the like.
The mixed solution for the selenization reaction consists of diselenide, yttrium trichloride and dichloromethane. Since dichloromethane contains chlorine, the solvation effect of the dichloromethane is favorable for improving the activity of the catalyst, but dichloromethane is a chlorine-containing compound which is less in toxicity, low in boiling point and easy to recycle, so that dichloromethane is used as a solvent in the mixed solution of the selenization reaction.
The diselenide is at least one of diphenyl diselenide, di-p-tolyl diselenide, di-p-fluorophenyl diselenide, di (3, 5-ditrifluoromethylphenyl) diselenide, di-n-butyl diselenide and di (2-pyridyl) diselenide. The reactive site is a selenium-selenium bond in diselenide.
In the mixed solution composed of diselenide, yttrium trichloride and dichloromethane, the concentration of diselenide is 0.01-0.06 mol/L, and the concentration of yttrium trichloride is 0.01-0.03 mmol/L. The concentration of diselenide is preferably 0.04 mol/L and the concentration of yttrium trichloride is preferably 0.02 mmol/L.
The selenization reaction is a heterogeneous reaction, and under the condition that the material is fully immersed in the precursor of the selenization liquid, the selenization effect is related to the concentration of the selenization reagent and is not related to the dosage of the selenization reagent. In the mixed solution, the concentration of diselenide is 0.01-0.06 mol/L, especially under the condition of 0.04 mol/L, the optimal selenizing effect can be achieved, and the effect of further improving the concentration of the selenizing solution on improving the selenium content in the material is not obvious.
In the mixed solution used in the selenization reaction, the concentration of yttrium trichloride is 0.01-0.03 mmol/L, preferably 0.02 mmol/L. At this concentration, it is sufficient to heterocleave the diselenide selenium-selenium bond and to react electrophilically with the benzene ring of the polystyrene. The use of too much catalyst is not beneficial to improve the selenization efficiency.
In addition, the preferred selenization reaction time of the present invention is 36 hours. During the time, the selenylation can be fully carried out, and the reaction efficiency is improved.
In the invention, the polystyrene needs to be soaked in cyclohexane for 12-36 hours in advance, wherein the soaking time is preferably 24 hours, and the soaking can swell the material, thereby being beneficial to the subsequent selenization reaction.
Compared with the prior art, the invention has the advantages that: (1) the selenium source is easy to obtain; (2) the selenization step is simple; (3) the selenizing condition is mild; (4) when the immobilized selenide material is synthesized, a functional group can be introduced to the material by changing a diselenide substituent group, so that the material has strong variability and is beneficial to subsequent performance regulation.
Detailed Description
The invention designs a method for selenizing polystyrene by using diselenide as a selenium source to prepare a corresponding immobilized selenide material. The reaction process is simple, the reaction condition is mild, and the method is suitable for large-scale application.
Example 1
The polystyrene selenization step is as follows: 100 g of polystyrene microspheres (100 meshes) with the crosslinking degree of 1 percent are soaked in cyclohexane for 24 hours (namely, the swelling process), the solution is filtered out, and the solution is dried for standby. 1 liter of dichloromethane mixed solution of 0.04 mol/L diphenyl diselenide and 0.02 mmol/L yttrium trichloride is prepared. And soaking the swelled polystyrene in the mixed solution of diphenyl diselenide and yttrium trichloride. After soaking in a large open beaker (2L) for 36 hours, filtration was carried out and the polystyrene microspheres were washed with cyclohexane. And drying in the air to obtain the selenized polystyrene material. The selenium content in the selenized polystyrene material is 0.42 percent through inductively coupled plasma mass spectrometry.
The selenized polystyrene material has certain catalytic activity, can be used for catalyzing the dihydroxylation of cyclohexene to prepare 1, 2-cyclohexanediol, and comprises the following steps: a20 mL reaction tube was charged with 100 mg of a selenized polystyrene catalyst and a magnetic stirrer. A solution containing 1 mL of cyclohexene acetonitrile (1 mol/L) and 1 mL of hydrogen peroxide acetonitrile (1 mol/L, prepared using 30% by mass hydrogen peroxide) was injected. Under magnetic stirring 80 oAfter heating for 10 hours, the reaction was stopped. The gas chromatography and mass spectrometry determination proves that the yield of the 1, 2-cyclohexanediol is 97 percent.
Example 2
The other conditions were the same as in example 1, but the swelling time of polystyrene in cyclohexane was different, and the effect of swelling time on selenization of the material was examined. The results are shown in Table 1.
TABLE 1 Effect of swelling time on selenization Process
| Numbering | Swelling time | Selenium content in the material |
| 1 | 12 hours | 0.11% |
| 2 | 18 hours | 0.35% |
| 3 | 24 hours (example 1) | 0.42% |
| 4 | 30 hours | 0.42% |
| 5 | 36 hours | 0.44% |
From the above, it can be seen that the swelling of polystyrene in cyclohexane for 24 hours is sufficient, and the effect of prolonging the swelling time on increasing the selenium content of the material is not obvious.
Example 3
Other conditions were the same as in example 1, and selenization was performed using diselenide at different concentrations, and the results are shown in table 2.
TABLE 2 Effect of diselenide concentration in the Mixed solution on the selenization reaction
| Numbering | Diselenide concentration in selenizing liquid | Selenium content in the material |
| 1 | 0.01 mol/L | 0.20% |
| 2 | 0.02 mol/L | 0.26% |
| 3 | 0.03 mol/L | 0.37 |
| 4 | 0.04 mol/L (example 1) | 0.42% |
| 5 | 0.05 mol/L | 0.44% |
| 6 | 0.06 mol/L | 0.45% |
From the above, the selenization reaction is facilitated by increasing the concentration of diselenide in the mixed solution. But after the diselenide concentration reaches 0.04 mol/L, the diselenide concentration is further improved, and the effect of improving the selenium content in the product is not obvious. From the viewpoint of cost, it is most preferable that the concentration of diselenide in the mixed solution is 0.04 mol/L.
Example 4
Other conditions were the same as in example 1, using different diselenides as the selenium source, and the results are shown in Table 3.
TABLE 3 Effect of different diselenides as selenium sources on the selenization reaction
| Numbering | Diselenide name | Diselenide CAS accession number | Selenium content in the material |
| 1 | Diphenyl diselenide (example 1) | 1666-13-3 | 0.42% |
| 2 | Di-p-tolyl diselenide | 21856-94-0 | 0.46% |
| 3 | Di-p-fluorophenyl diselenide | 52673-29-7 | 0.35% |
| 4 | Bis (3, 5-bistrifluoromethylphenyl) diselenide | 335383-23-8 | 0.31% |
| 5 | Di-n-butyl diselenide | 20333-40-8 | 0.48% |
| 6 | Bis (2-pyridyl) diselenides | 59957-75-4 | 0.51% |
Diselenide is a readily available compound that can be purchased directly or prepared from the corresponding halohydrocarbon by means of Grignard reagent insertion, acidification, oxidation. For details, see the literature: appl. organic. chem. 2014, 28, 652-656.
The above results show that polystyrene can be selenized using various diselenides. Among them, the electron-deficient diselenides (e.g., nos. 3 and 4) are slightly inferior in effect. This is related to the selenization principle: the lone pair electron of selenium in diselenide firstly coordinates with metal yttrium, thereby inducing heterolytic splitting of selenium-selenium bond, generating selenium positive ion, and further carrying out electrophilic substitution reaction with benzene ring in polystyrene. In the electron-deficient diselenide, the lone pair on selenium is not easy to give out, so that the selenizing effect is slightly poor.
Example 5
Other conditions were the same as in example 1, and different concentrations of yttrium trichloride were used to catalyze the selenization reaction, and the results are shown in table 4.
TABLE 4 Effect of different concentrations of Yttrium trichloride on the selenization reaction
| Numbering | Concentration of yttrium trichloride | Selenium content in the material |
| 1 | 0.01 mmol/L | 0.23% |
| 2 | 0.015 mmol/L | 0.36% |
| 3 | 0.02 mmol/L (example 1) | 0.42% |
| 4 | 0.025 mmol/L | 0.45% |
| 5 | 0.03 mmol/L | 0.44% |
As can be seen from the above, 0.02 mmol/L yttrium trichloride can well satisfy the reaction requirement. The catalyst concentration is further increased, and the selenization reaction is not obviously improved. From the viewpoint of cost, yttrium trichloride is preferably used at a concentration of 0.02 mmol/L.
Example 6
Other conditions the same as example 1, the effect of the selenization reaction time on the selenization of the material was examined and the results are shown in table 5.
TABLE 5 Effect of selenization reaction time on material selenization
| Numbering | Reaction time of selenization | Selenium content in the material |
| 1 | 24 hours | 0.31% |
| 2 | 30 hours | 0.39% |
| 3 | 36 hours (example 1) | 0.42% |
| 4 | 42 hours | 0.42% |
| 5 | 48 hours | 0.43% |
From the above, the selenization reaction is almost stopped in 36 hours, and the improvement of the selenization degree by prolonging the time has no obvious effect.
Claims (6)
1. A method for selenizing polystyrene by taking diselenide as a selenium source is characterized in that the polystyrene is soaked in cyclohexane for 12-36 hours, then is filtered out and dried, and then is placed in a mixed solution composed of diselenide, yttrium trichloride and dichloromethane for a selenization reaction for 24-48 hours, so that the selenized polystyrene is obtained.
2. The method for selenizing polystyrene, which uses diselenide as a selenium source, according to claim 1, wherein the diselenide is at least one of diphenyl diselenide, di-p-tolyl diselenide, di-p-fluorophenyl diselenide, bis (3, 5-bistrifluoromethylphenyl) diselenide, di-n-butyl diselenide, and bis (2-pyridyl) diselenide.
3. The method for selenizing the polystyrene by using the diselenide as the selenium source according to claim 1 or 2, wherein in the mixed solution consisting of the diselenide, the yttrium trichloride and the dichloromethane, the concentration of the diselenide is 0.01-0.06 mol/L, and the concentration of the yttrium trichloride is 0.01-0.03 mmol/L.
4. The method for selenizing polystyrene with diselenide as a selenium source according to claim 3, wherein the concentration of diselenide is 0.04 mol/L and the concentration of yttrium trichloride is 0.02 mmol/L in the mixed solution consisting of diselenide, yttrium trichloride and dichloromethane.
5. The method for selenizing polystyrene with diselenide as the selenium source as claimed in claim 1 or 2, wherein the reaction time for the selenization is 36 hours.
6. The method for selenizing polystyrene, using diselenide as the selenium source, according to claim 1 or 2, characterized in that the soaking of polystyrene in cyclohexane is 24 hours.
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| TAE SEOK KWON ET AL.: "Living Radical Polymerization of Styrene with Diphenyl Diselenide as a Photoiniferter. Synthesis of Polystyrene with Carbon-Carbon Double Bonds at Both Chain Ends", JOURNAL OF MACROMOLECULAR SCIENCE, PART A PURE AND APPLIED CHEMISTRY, vol. 34, no. 9, pages 1553 - 1567 * |
| 俞磊等: "二苯基二硒醚催化双氧水氧化环己烯合成1, 2-环己二醇", 有机化学, vol. 33, no. 5, pages 1096 - 1099 * |
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