CN109589998A - A kind of novel ZnO/Se/SiO2It the preparation method of composite material and its is applied in preparing phthalide - Google Patents
A kind of novel ZnO/Se/SiO2It the preparation method of composite material and its is applied in preparing phthalide Download PDFInfo
- Publication number
- CN109589998A CN109589998A CN201910038448.5A CN201910038448A CN109589998A CN 109589998 A CN109589998 A CN 109589998A CN 201910038448 A CN201910038448 A CN 201910038448A CN 109589998 A CN109589998 A CN 109589998A
- Authority
- CN
- China
- Prior art keywords
- zno
- composite material
- sio
- preparation
- phthalide
- 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.)
- Granted
Links
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 239000002131 composite material Substances 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 229910052681 coesite Inorganic materials 0.000 claims abstract description 16
- 229910052906 cristobalite Inorganic materials 0.000 claims abstract description 16
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052682 stishovite Inorganic materials 0.000 claims abstract description 16
- 229910052905 tridymite Inorganic materials 0.000 claims abstract description 16
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000001914 filtration Methods 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 239000000706 filtrate Substances 0.000 claims abstract description 6
- 239000011669 selenium Substances 0.000 claims description 41
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 238000003756 stirring Methods 0.000 claims description 21
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 15
- 229910052711 selenium Inorganic materials 0.000 claims description 15
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 12
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 6
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 6
- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- 230000001376 precipitating effect Effects 0.000 claims description 6
- 238000010792 warming Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 claims 1
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 37
- 239000011787 zinc oxide Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- JKGITWJSGDFJKO-UHFFFAOYSA-N ethoxy(trihydroxy)silane Chemical compound CCO[Si](O)(O)O JKGITWJSGDFJKO-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/057—Selenium or tellurium; Compounds thereof
- B01J27/0573—Selenium; Compounds thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Silicon Compounds (AREA)
Abstract
The present invention relates to a kind of novel ZnO/Se/SiO2It the preparation method of composite material and its is applied in preparing phthalide, the preparation method of the phthalide includes the following steps: for o-toluic acid to be dissolved in organic solvent, and ZnO/Se/SiO is added2ZnO/Se/SiO is recovered by filtration after being stirred to react 20-24 hours at room temperature in composite material2Composite material, filtrate concentration remove organic solvent to get phthalide.
Description
Technical field
The invention belongs to Material Fields, and in particular to a kind of novel ZnO/Se/SiO2The preparation method of composite material and its
It is applied in preparing phthalide.
Background technique
Zinc oxide (ZnO) particle has many advantages, such as that large specific surface area, chemical property are stablized, and is widely used in photochemical catalyst
Field.Selenium (Se) has many excellent physicochemical properties as a kind of intrinsic p-type semiconductor material.There has been no ZnO/ at present
Report of the Se composite material in terms of organic reaction catalyst.It is zinc source, SiO that applicant utilizes zinc nitrate in the recent period2For carrier, system
A kind of standby novel ZnO/Se/SiO2Composite material, the material can be used as oxidant for oxidation reaction, expand for further research
Open up ZnO/Se/SiO2The purposes of composite material, the present invention provide ZnO/Se/SiO2Composite material is in catalysis o-toluic acid system
Application in standby phthalide.
Summary of the invention
The present invention provides a kind of novel ZnO/Se/SiO2The preparation method of composite material, it is characterised in that including walking as follows
It is rapid:
Under stirring, the hydrazine hydrate containing selenium is added into zinc nitrate solution for room temperature, continues after stirring 20-30min, is warming up to
After 170-180 DEG C of reaction 8-12h, ethyl orthosilicate is added after naturally cooling to 90 DEG C, continues to stir to cooled to room temperature,
Filtering, precipitating are successively washed with deionized water, dehydrated alcohol, are dried in vacuo up to the novel ZnO/Se/SiO2Composite material.
The wherein preferred 0.1-0.2mmol/mL of the concentration of zinc nitrate solution, every mM of zinc nitrate use hydrazine hydrate containing selenium
1.0-1.5mL;The hydrazine hydrate containing selenium is 6-10mg containing selenium in every milliliter of hydrazine hydrate;Every mM of zinc nitrate uses positive silicic acid
Ethyl ester 150-200 μ L;Above-mentioned reaction preferably carries out in a high pressure reaction kettle.
Another embodiment of the present invention provides above-mentioned novel ZnO/Se/SiO2Composite material is in catalysis o-toluic acid
Prepare the application in phthalide.
Another embodiment of the present invention provides a kind of preparation method of phthalide, it is characterised in that includes the following steps:
O-toluic acid is dissolved in organic solvent, above-mentioned ZnO/Se/SiO is added2Composite material, stirring is anti-at room temperature
After answering 20-24 hours, ZnO/Se/SiO is recovered by filtration2Composite material, filtrate concentration remove organic solvent to get phthalide;Every milli
It is preferable to use ZnO/Se/SiO for mole o-toluic acid2Composite material 10-15mg;The preferred methylene chloride of the organic solvent,
One or more of chloroform, ether, THF.
Compared with the prior art, the advantages of the present invention are as follows: (1) present invention using zinc nitrate as zinc source, SiO2For carrier, system
A kind of standby novel ZnO/Se/SiO2Composite material, the material can be used for being catalyzed o-toluic acid and prepare phthalide;(2) this hair
The ZnO/Se/SiO of bright preparation2Secondary use can be recycled in composite material.
Detailed description of the invention
Fig. 1 is the SEM figure (right side) of product A and the TEM figure (left side) of product A;
Fig. 2 is the XRD diagram of product A.
Specific embodiment
For the ease of a further understanding of the present invention, examples provided below has done more detailed description to it.But
It is that these embodiments are only not supposed to be a limitation to the present invention or implementation principle for better understanding invention, reality of the invention
The mode of applying is not limited to the following contents.
Embodiment 1
Room temperature, under stirring, to the hydrazine hydrate containing selenium is added in zinc nitrate solution (0.1mmol/mL, 100mL), (10mL contains
Selenium 100mg), continue after stirring 20min, after being warming up to 170 DEG C (autoclave) reaction 12h, adds after naturally cooling to 90 DEG C
Enter ethyl orthosilicate (1.5mL), continues stirring to cooled to room temperature, filtering, precipitating successively use deionized water, dehydrated alcohol
It washs, be dried in vacuo up to the ZnO/Se/SiO2Composite material (hereinafter referred to as product A, Fig. 1,2).
Embodiment 2
Room temperature, under stirring, to the hydrazine hydrate containing selenium is added in zinc nitrate solution (0.2mmol/mL, 100mL), (30mL contains
Selenium 180mg), continue after stirring 30min, after being warming up to 180 DEG C (autoclave) reaction 8h, is added after naturally cooling to 90 DEG C
Ethyl orthosilicate (4.0mL) continues stirring to cooled to room temperature, and filtering, precipitating are successively washed with deionized water, dehydrated alcohol
It washs, be dried in vacuo up to the ZnO/Se/SiO2Composite material (hereinafter referred to as product B, SEM figure are consistent with product A).
Embodiment 3
Room temperature, under stirring, to the hydrazine hydrate containing selenium is added in zinc nitrate solution (0.1mmol/mL, 100mL), (10mL contains
Selenium 100mg), continue after stirring 20min, after being warming up to 170 DEG C (autoclave) reaction 12h, cooled to room temperature, mistake
Filter, precipitating are successively washed with deionized water, dehydrated alcohol, are dried in vacuo up to ZnO/Se composite material (hereinafter referred to as products C).
Embodiment 4
Room temperature under stirring, is added hydrazine hydrate (10mL) in zinc nitrate solution (0.1mmol/mL, 100mL), continues to stir
After 20min, after being warming up to 170 DEG C (autoclave) reaction 12h, ethyl orthosilicate is added after naturally cooling to 90 DEG C
(1.5mL) continues stirring to cooled to room temperature, and filtering, precipitating is successively washed with deionized water, dehydrated alcohol, vacuum is done
Dry ZnO/SiO to obtain the final product2Composite material (hereinafter referred to as product D).
Embodiment 5
O-toluic acid (1mmol) is dissolved in methylene chloride (8mL), is added product A (15mg), stirring is anti-at room temperature
After answering 20 hours, be recovered by filtration product A, filtrate concentration remove methylene chloride to get phthalide (125mg, yield are about 93.2%,
HPLC purity 92.5%,1H、13C NMR data and report are consistent).
Embodiment 6
O-toluic acid (1mmol) is dissolved in THF (6mL), is added product B (10mg), is stirred to react 24 at room temperature
After hour, product B is recovered by filtration, filtrate concentration removes THF, and (129mg, yield are about 96.2%, HPLC purity to get phthalide
90.2%,1H、13C NMR data and report are consistent).
Embodiment 7
O-toluic acid (1mmol) is dissolved in methylene chloride (8mL), is added products C (15mg), stirring is anti-at room temperature
After answering 20 hours, the content that HPLC detects reaction solution o-toluic acid is 86.2%.
Embodiment 8
O-toluic acid (1mmol) is dissolved in methylene chloride (8mL), is added product D (15mg), stirring is anti-at room temperature
After answering 20 hours, the content that HPLC detects reaction solution o-toluic acid is 97.3%.
Embodiment 9
O-toluic acid (1mmol) is dissolved in methylene chloride (8mL), the product A that embodiment 1 recycles, room temperature is added
Under be stirred to react 20 hours after, be recovered by filtration product A, filtrate concentration removes methylene chloride, and (116mg, yield are about to get phthalide
86.5%, HPLC purity 89.1%).
Claims (9)
1. a kind of preparation method of phthalide, it is characterised in that include the following steps:
O-toluic acid is dissolved in organic solvent, ZnO/Se/SiO is added2It is small to be stirred to react 20-24 at room temperature for composite material
ZnO/Se/SiO is recovered by filtration in Shi Hou2Composite material, filtrate concentration remove organic solvent to get phthalide.
2. preparation method described in claim 1, it is characterised in that it is preferable to use ZnO/Se/ for every mM of o-toluic acid
SiO2Composite material 10-15mg.
3. the described in any item preparation methods of claim 1-2, it is characterised in that the preferred methylene chloride of the organic solvent, chlorine
One or more of imitative, ether, THF.
4. the described in any item preparation methods of claim 1-3, it is characterised in that the ZnO/Se/SiO2The preparation of composite material
Method includes the following steps: room temperature, and under stirring, the hydrazine hydrate containing selenium is added into zinc nitrate solution, continues to stir 20-30min
Afterwards, after being warming up to 170-180 DEG C of reaction 8-12h, ethyl orthosilicate is added after naturally cooling to 90 DEG C, continues to stir to naturally cold
But to room temperature, filtering, precipitating are successively washed with deionized water, dehydrated alcohol, are dried in vacuo up to the ZnO/Se/SiO2It is compound
Material.
5. preparation method as claimed in claim 4, it is characterised in that the preferred 0.1-0.2mmol/mL of the concentration of zinc nitrate solution, often
MM zinc nitrate uses the 1.0-1.5mL of hydrazine hydrate containing selenium;The hydrazine hydrate containing selenium is 6- containing selenium in every milliliter of hydrazine hydrate
10mg。
6. the described in any item preparation methods of claim 4-5, it is characterised in that every mM of zinc nitrate uses ethyl orthosilicate
150-200μL。
7. a kind of ZnO/Se/SiO2The preparation method of composite material, it is characterised in that described in any item including claim 4-6
Preparation method and step.
8. the described in any item ZnO/Se/SiO of claim 1-32Composite material is prepared in cyclohexanedione in oxidation cyclohexanediol
Using.
9. the ZnO/Se/SiO of the described in any item preparation method preparations of claim 4-62Composite material is in catalysis o-methyl-benzene first
Acid prepares the application in phthalide.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910038448.5A CN109589998B (en) | 2019-01-15 | 2019-01-15 | Novel ZnO/Se/SiO2Preparation method of composite material and application of composite material in preparation of phthalide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910038448.5A CN109589998B (en) | 2019-01-15 | 2019-01-15 | Novel ZnO/Se/SiO2Preparation method of composite material and application of composite material in preparation of phthalide |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109589998A true CN109589998A (en) | 2019-04-09 |
CN109589998B CN109589998B (en) | 2021-09-03 |
Family
ID=65965190
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910038448.5A Active CN109589998B (en) | 2019-01-15 | 2019-01-15 | Novel ZnO/Se/SiO2Preparation method of composite material and application of composite material in preparation of phthalide |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN109589998B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110498783A (en) * | 2019-08-02 | 2019-11-26 | 成都蓝蜻蜓生物技术有限公司 | A method of his intermediate of synthesis Luo Shasi |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6147227A (en) * | 1996-10-01 | 2000-11-14 | Basf Aktiengesellschaft | Process for preparing phthalides |
CN101020627A (en) * | 2007-01-22 | 2007-08-22 | 河北大学 | Process of synthesizing 1,4-cyclohexyl dione |
CN101302209A (en) * | 2008-06-13 | 2008-11-12 | 浙江工业大学 | Method for preparing phthalide by benzoic anhydride liquid phase hydrogenation with gold-base catalyst |
JP2015142882A (en) * | 2014-01-31 | 2015-08-06 | 博 久保田 | Hydrogen formation catalyst |
CN105753768A (en) * | 2014-12-15 | 2016-07-13 | 北京恒瑞新霖科技有限公司 | Production method of single nitrogenous heterocyclic ring-containing compound |
CN106588618A (en) * | 2016-10-28 | 2017-04-26 | 江苏扬农化工集团有限公司 | Method for catalyzing oxidation of phenol and hydrogen peroxide with selenium-containing catalyst for synthesis of p-benzoquinone |
CN107321375A (en) * | 2017-07-13 | 2017-11-07 | 扬州工业职业技术学院 | A kind of SiO2/ZnO/g‑C3N4Nano material and its application in reduction of hexavalent chromium |
WO2018109247A1 (en) * | 2016-12-15 | 2018-06-21 | Consejo Superior De Investigaciones Científicas (Csic) | Regioselective, stereoselective and catalytic hydrochlorination of alkynes |
-
2019
- 2019-01-15 CN CN201910038448.5A patent/CN109589998B/en active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6147227A (en) * | 1996-10-01 | 2000-11-14 | Basf Aktiengesellschaft | Process for preparing phthalides |
CN101020627A (en) * | 2007-01-22 | 2007-08-22 | 河北大学 | Process of synthesizing 1,4-cyclohexyl dione |
CN101302209A (en) * | 2008-06-13 | 2008-11-12 | 浙江工业大学 | Method for preparing phthalide by benzoic anhydride liquid phase hydrogenation with gold-base catalyst |
JP2015142882A (en) * | 2014-01-31 | 2015-08-06 | 博 久保田 | Hydrogen formation catalyst |
CN105753768A (en) * | 2014-12-15 | 2016-07-13 | 北京恒瑞新霖科技有限公司 | Production method of single nitrogenous heterocyclic ring-containing compound |
CN106588618A (en) * | 2016-10-28 | 2017-04-26 | 江苏扬农化工集团有限公司 | Method for catalyzing oxidation of phenol and hydrogen peroxide with selenium-containing catalyst for synthesis of p-benzoquinone |
WO2018109247A1 (en) * | 2016-12-15 | 2018-06-21 | Consejo Superior De Investigaciones Científicas (Csic) | Regioselective, stereoselective and catalytic hydrochlorination of alkynes |
CN107321375A (en) * | 2017-07-13 | 2017-11-07 | 扬州工业职业技术学院 | A kind of SiO2/ZnO/g‑C3N4Nano material and its application in reduction of hexavalent chromium |
Non-Patent Citations (2)
Title |
---|
LEI WANG ET AL.: ""One-step electrochemical synthesis and photoelectric conversion of a ZnO/Se/RGO composite"", 《SEMICOND. SCI. TECHNOL.》 * |
张昊 等: ""Se掺杂ZnO的晶体结构和电子性质的第一性原理计算"", 《原子与分子物理学报》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110498783A (en) * | 2019-08-02 | 2019-11-26 | 成都蓝蜻蜓生物技术有限公司 | A method of his intermediate of synthesis Luo Shasi |
Also Published As
Publication number | Publication date |
---|---|
CN109589998B (en) | 2021-09-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN110669756B (en) | Protein and polysaccharide doped metal organic framework compound and preparation method thereof | |
CN109589998A (en) | A kind of novel ZnO/Se/SiO2It the preparation method of composite material and its is applied in preparing phthalide | |
CN1863808B (en) | Penam crystal and process for producing the same | |
CN113181967B (en) | Application of sulfonated titanium modified KIT-6 solid acid catalyst in borneol synthesis | |
CN102584686B (en) | Water soluble terpyridyl fluorescent compound and preparation method thereof | |
CN108912143A (en) | A kind of preparation method of Tazobactam Sodium benzhydryl ester intermediate | |
Xu et al. | Open-cage fullerene with a stopper acts as a molecular vial for a single water molecule | |
CN114957207B (en) | Application of water-soluble photocatalyst in photocatalytic reaction | |
CN109608349B (en) | Green preparation method of magnesium glycinate | |
CN108031476B (en) | Catalyst for preparing β -ionone, preparation method thereof and method for preparing β -ionone by using catalyst | |
CN109665951A (en) | A kind of ZnO/Se/SiO2Composite material and its application as oxidant | |
CN102993131B (en) | Method for utilizing o-chlorocyclohexanol to prepare cyclohexene oxide by cyclization | |
CN104892370A (en) | Preparation method for reductive coenzyme Q10 | |
CN114522733A (en) | Method for preparing nano composite material by using bond breaking strategy and application of nano composite material in CO catalysis2Application in ethynylation reaction | |
CN113621672A (en) | Novel method for preparing dehydroepiandrosterone | |
CN114029082A (en) | Synthesis method and application of novel high-activity magnetic nanoparticles | |
CN110041274B (en) | Method for preparing 5-fluoroalkyl triazole compound by air oxidation multi-component one-pot method | |
CN103819489B (en) | A kind of preparation method of benzhydryl s-oxopenicillanate | |
CN112574043A (en) | Production process of alkaline red intermediate 3-ethylaminop-methylphenol | |
CN111925333A (en) | Preparation method, product and application of 2-amino-5-methylpyrazine | |
CN107311862B (en) | Preparation method of sitagliptin intermediate | |
CN113831387B (en) | Preparation method of finasteride isomer 17 alpha-finasteride | |
CN109467523A (en) | A kind of green synthesis method of the third sulfonic acid chloride of 3- chlorine | |
CN113999101B (en) | Synthesis method of anthraquinone derivative SZ-685C | |
CN109516898B (en) | Method for artificially synthesizing resveratrol |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |