CN112028910B - Preparation method of high-purity dimethyl zinc - Google Patents
Preparation method of high-purity dimethyl zinc Download PDFInfo
- Publication number
- CN112028910B CN112028910B CN202010794418.XA CN202010794418A CN112028910B CN 112028910 B CN112028910 B CN 112028910B CN 202010794418 A CN202010794418 A CN 202010794418A CN 112028910 B CN112028910 B CN 112028910B
- Authority
- CN
- China
- Prior art keywords
- zinc
- organic solvent
- prepare
- solution
- grignard reagent
- 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.)
- Active
Links
- AXAZMDOAUQTMOW-UHFFFAOYSA-N dimethylzinc Chemical compound C[Zn]C AXAZMDOAUQTMOW-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 32
- -1 methyl halide Chemical class 0.000 claims abstract description 22
- 239000011592 zinc chloride Substances 0.000 claims abstract description 16
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 16
- 238000010992 reflux Methods 0.000 claims abstract description 14
- 239000007818 Grignard reagent Substances 0.000 claims abstract description 13
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000004795 grignard reagents Chemical class 0.000 claims abstract description 13
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 13
- 239000011777 magnesium Substances 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 239000012535 impurity Substances 0.000 claims abstract description 8
- 238000001514 detection method Methods 0.000 claims abstract description 7
- 238000004821 distillation Methods 0.000 claims abstract description 7
- 238000001816 cooling Methods 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 230000005311 nuclear magnetism Effects 0.000 claims abstract description 5
- 238000005070 sampling Methods 0.000 claims abstract description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 9
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 6
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 238000005086 pumping Methods 0.000 claims description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- 239000002994 raw material Substances 0.000 abstract description 9
- 229910052725 zinc Inorganic materials 0.000 abstract description 8
- 239000011701 zinc Substances 0.000 abstract description 8
- 229910052751 metal Inorganic materials 0.000 abstract description 5
- 239000002184 metal Substances 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000009616 inductively coupled plasma Methods 0.000 description 4
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 229910002601 GaN Inorganic materials 0.000 description 2
- JMASRVWKEDWRBT-UHFFFAOYSA-N Gallium nitride Chemical compound [Ga]#N JMASRVWKEDWRBT-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 2
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- GNLJBJNONOOOQC-UHFFFAOYSA-N $l^{3}-carbane;magnesium Chemical compound [Mg]C GNLJBJNONOOOQC-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 238000002488 metal-organic chemical vapour deposition Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XCZXGTMEAKBVPV-UHFFFAOYSA-N trimethylgallium Chemical compound C[Ga](C)C XCZXGTMEAKBVPV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P10/00—Technologies related to metal processing
- Y02P10/20—Recycling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention provides a preparation method of high-purity dimethyl zinc, which comprises the following steps: 1. adding a methyl halide solution into a mixture of magnesium chips and an organic solvent under anhydrous and anaerobic conditions to prepare a Grignard reagent; 2. dissolving zinc chloride by using an organic solvent to prepare a zinc chloride solution; 3. dropwise adding zinc chloride solution into the Grignard reagent, heating and refluxing for 12 hours, and reacting to prepare dimethyl zinc solution; 4. cooling after the reflux is finished, and then, replacing the normal pressure distillation device with a receiving device, cooling the receiving device by liquid nitrogen, and controlling the temperature to be 150-160 ℃ to receive the product; 5. and (5) sampling and analyzing, and performing nuclear magnetism detection and Icp detection on the product. The alkyl zinc is prepared by adopting the reaction of excessive Grignard reagent and metal zinc halide, the cost is low, the reaction efficiency is poor, the safety is high, the introduction of organic impurities is difficult, the synthesis does not need harsh reaction conditions, the raw materials are cheap, and the operation is simple.
Description
Technical Field
The invention relates to the field of metal organic synthesis, in particular to a preparation method of high-purity dimethyl zinc.
Background
In recent years, semiconductor materials have been rapidly developed, wherein gallium nitride materials, by virtue of their wide direct band gap and high thermal conductivity, are widely used in high power optoelectronic devices. Zinc oxide is a new generation of short wavelength semiconductor photoelectric material after gallium nitride, and the zinc oxide wide forbidden band semiconductor material has wide application prospect and has great application prospect in the fields of sensors, batteries, ultraviolet photoelectric detection, lasers and the like. The high-purity dimethyl zinc is used as a precursor raw material of zinc oxide, is the most important raw material of semiconductor laser doping and thin film solar cells at present, and has gradually increased demands in the integrated circuit industry, and the dimethyl zinc is also commonly used for preparing organic compounds containing methyl or preparing methyl metal compounds, and is mainly used for preparing II-VI group compound semiconductors on MOCVD. There are two schemes for preparing dimethyl zinc: firstly, trimethyl aluminum and zinc chloride are reacted and diethyl zinc is added, the raw materials of the scheme are expensive, and the product contains more trimethyl aluminum and diethyl zinc organic impurities, so that the purification is not easy; secondly, dimethyl aluminum chloride is used as a raw material, diethyl zinc is added to generate dimethyl zinc under heating conditions, and colorless and transparent dimethyl zinc is obtained through normal-pressure rectification separation, but the dimethyl aluminum chloride is a byproduct of preparing trimethyl gallium, and the raw material is not easy to obtain and causes gallium pollution, so that the preparation of the dimethyl zinc is limited, and meanwhile, the preparation cost of the dimethyl zinc is greatly increased. It becomes important to solve this problem.
Disclosure of Invention
The invention aims to provide a preparation method of high-purity dimethyl zinc, which adopts excessive Grignard reagent and metal zinc halide to react to prepare alkyl zinc, so that the problems of high price of raw materials and severe preparation conditions for preparing the high-purity dimethyl zinc are reduced.
The invention provides a preparation method of high-purity dimethyl zinc, which comprises the following steps: 1. adding a methyl halide solution into a mixture of magnesium chips and an organic solvent under anhydrous and anaerobic conditions to prepare a Grignard reagent; 2. dissolving zinc chloride by using an organic solvent to prepare a zinc chloride solution; 3. dropwise adding zinc chloride solution into the Grignard reagent, heating and refluxing for 12 hours, and reacting to prepare dimethyl zinc solution; 4. cooling after the reflux is finished, and then, replacing the normal pressure distillation device with a receiving device, cooling the receiving device by liquid nitrogen, and controlling the temperature to be 150-160 ℃ to receive the product; 5. and (5) sampling and analyzing, and performing nuclear magnetism detection and Icp detection on the product.
The further improvement is that: in the step 1 and the step 2, the organic solvent adopts one of n-butyl ether and diethylene glycol dimethyl ether, the water and impurity removal treatment is carried out before the organic solvent is used, anhydrous calcium chloride is added into the organic solvent, and the mixture is stirred for 2 hours and filtered for use.
The further improvement is that: and (3) drying and dewatering the magnesium chips before using the magnesium chips in the step (1), heating the magnesium chips to 100 ℃ and extracting the magnesium chips for 2 hours under absolute pressure.
The further improvement is that: in the step 1, methyl iodide is adopted as the methyl halide, molecular sieve is added before the methyl halide is used for removing water, and the methyl halide is used after filtration.
The further improvement is that: before the zinc chloride is used in the step 2, the sulfoxide chloride is added for heating and refluxing for 2 hours, and then the heating absolute pressure is used for pumping the sulfoxide chloride.
The invention has the beneficial effects that: the alkyl zinc is prepared by adopting excessive Grignard reagent and metal zinc halide for reaction, and has the advantages of low cost, poor reaction efficiency, high safety, difficult introduction of organic impurities, no need of harsh reaction conditions for synthesis, cheap raw materials and simple operation.
Description of the embodiments
The present invention will be further described in detail with reference to examples, which are provided for the purpose of illustration only and are not intended to limit the scope of the present invention. Example 1
The embodiment provides a preparation method of high-purity dimethyl zinc, which comprises the following steps:
1. 2.75mol of magnesium chips and 1000ml of n-butyl ether are added into a 2L two-mouth bottle, and the two-mouth bottle is put into a normal pressure reflux device and stirred; 2.5mol of methyl iodide is dripped into the two bottles, the temperature of the bottom bottle is rapidly increased with a small amount of reflux, and after the methyl iodide is dripped, stirring is maintained for 1h, so as to obtain a Grignard reagent: methyl magnesium n-butyl ether solution;
2. dissolving 1.2mol of zinc chloride by 400ml of n-butyl ether to prepare zinc chloride n-butyl ether solution, slowly dripping the zinc chloride n-butyl ether solution into the methyl magnesium iodide n-butyl ether solution in the step 1, simultaneously carrying out rapid stirring, controlling the temperature to be 60 ℃, keeping the temperature to be 60 ℃ for reflux for 12 hours after dripping is finished, and finishing the reaction;
3. and (3) placing the liquid in an atmospheric distillation device, performing atmospheric distillation, wherein the temperature of a bottom bottle is controlled to be 150-160 ℃, the condensing temperature is controlled to be-20-10 ℃, the temperature of a liquid nitrogen receiving device is controlled to be-60-50 ℃, distilling to obtain colorless transparent liquid, weighing 97.1g, and detecting the nuclear magnetism and ICP of the product.
The material yield in the case is 85%, wherein n-butyl ether can be recycled, and the product is detected by a JNM-ECZ400S nuclear magnetic resonance spectrometer: 1HNMR (400 MHz, C6D 6) delta: -0.67 (s, 6H), without impurity peaks; an inductively coupled plasma emission spectrometer (Optima 8000) detects inorganic elements <1ppm with a purity of up to 6N.
Examples
The embodiment provides a preparation method of high-purity dimethyl zinc, which comprises the following steps:
1. adding 4.2mol of magnesium chips and 1500ml of diethylene glycol dimethyl ether into a 3L two-port bottle, putting the mixture into a normal pressure reflux device, and starting stirring; 3.75mol of methyl iodide is dripped into the two bottles, the temperature of the bottom bottle is rapidly increased with a small amount of reflux, and after the methyl iodide is dripped, stirring is maintained for 1h, so as to obtain a Grignard reagent: methyl magnesium iodide diethylene glycol dimethyl ether solution;
2. 1.8mol of zinc chloride is dissolved by 600ml of diethylene glycol dimethyl ether to prepare a zinc chloride diethylene glycol dimethyl ether solution, the zinc chloride diethylene glycol dimethyl ether solution is slowly dripped into the methyl magnesium iodide diethylene glycol dimethyl ether solution in the step 1, meanwhile, the quick stirring is carried out, the temperature is controlled at 60 ℃, the reflux is kept at 60 ℃ for 12 hours after the dripping is finished, and the reaction is finished;
3. and (3) placing the liquid in an atmospheric distillation device, performing atmospheric distillation, wherein the temperature of a bottom bottle is controlled to be 150-160 ℃, the condensing temperature is controlled to be-20-10 ℃, the temperature of a liquid nitrogen receiving device is controlled to be-60-50 ℃, distilling to obtain colorless transparent liquid, weighing 149.5g, and detecting the nuclear magnetism and ICP of the product.
The material yield in the case is 87%, wherein diethylene glycol dimethyl ether can be recycled, and the product is detected by a JNM-ECZ400S nuclear magnetic resonance spectrometer: 1HNMR (400 MHz, C6D 6) delta, -0.67 (s, 6H), no impurity peak; an inductively coupled plasma emission spectrometer (Optima 8000) detects inorganic elements <1ppm with a purity of up to 6N.
The Grignard reagent preparation reaction formula is:
the reaction equation for preparing the dimethyl zinc is as follows:
the alkyl zinc is prepared by adopting the reaction of excessive Grignard reagent and metal zinc halide, the cost is low, the reaction efficiency is poor, the safety is high, the introduction of organic impurities is difficult, the synthesis does not need harsh reaction conditions, the raw materials are cheap, and the operation is simple.
Claims (3)
1. The preparation method of the high-purity dimethyl zinc is characterized by comprising the following steps of: 1. adding a methyl halide solution into a mixture of magnesium chips and an organic solvent under anhydrous and anaerobic conditions to prepare a Grignard reagent; 2. dissolving zinc chloride by using an organic solvent to prepare a zinc chloride solution; 3. dropwise adding zinc chloride solution into the Grignard reagent, heating and refluxing for 12 hours, and reacting to prepare dimethyl zinc solution; 4. cooling after the reflux is finished, and then, replacing the normal pressure distillation device with a receiving device, cooling the receiving device by liquid nitrogen, and controlling the temperature to be 150-160 ℃ to receive the product; 5. sampling analysis, and performing nuclear magnetism detection and ICP detection on the product; the organic solvent in the step 1 and the step 2 adopts one of n-butyl ether and diethylene glycol dimethyl ether, the water and impurity removal treatment is carried out before the organic solvent is used, anhydrous calcium chloride is added into the organic solvent, and the mixture is stirred for 2 hours and filtered for use; in the step 1, methyl iodide is adopted as the methyl halide, molecular sieve is added before the methyl halide is used for removing water, and the methyl halide is used after filtration.
2. The method for preparing high-purity dimethyl zinc according to claim 1, wherein the method comprises the following steps: and (3) drying and dewatering the magnesium chips before using the magnesium chips in the step (1), heating the magnesium chips to 100 ℃ and extracting the magnesium chips for 2 hours under absolute pressure.
3. The method for preparing high-purity dimethyl zinc according to claim 1, wherein the method comprises the following steps: before the zinc chloride is used in the step 2, the sulfoxide chloride is added for heating and refluxing for 2 hours, and then the heating absolute pressure is used for pumping the sulfoxide chloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010794418.XA CN112028910B (en) | 2020-08-10 | 2020-08-10 | Preparation method of high-purity dimethyl zinc |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010794418.XA CN112028910B (en) | 2020-08-10 | 2020-08-10 | Preparation method of high-purity dimethyl zinc |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112028910A CN112028910A (en) | 2020-12-04 |
| CN112028910B true CN112028910B (en) | 2023-06-30 |
Family
ID=73577781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010794418.XA Active CN112028910B (en) | 2020-08-10 | 2020-08-10 | Preparation method of high-purity dimethyl zinc |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112028910B (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3480654A (en) * | 1965-03-12 | 1969-11-25 | Goldschmidt Ag Th | Process for preparing organo-tin, -boron, -aluminum, -silicon, -phosphorous,-zinc and -mercury compounds |
| WO1993010124A1 (en) * | 1991-11-19 | 1993-05-27 | Air Products And Chemicals, Inc. | Process for the preparation of di-alkyl compounds of group 2b metals |
| TW200745144A (en) * | 2006-04-24 | 2007-12-16 | Ube Industries | High purity diisopropyl zinc and its method for manufacture |
| CN104774214A (en) * | 2015-04-28 | 2015-07-15 | 河南承明光电新材料股份有限公司 | Preparation method for dimethylzinc |
| CN105669722A (en) * | 2016-03-02 | 2016-06-15 | 南京大学 | Method for preparing high-purity dimethylzine by utilizing prepared trimethyl gallium by-product |
-
2020
- 2020-08-10 CN CN202010794418.XA patent/CN112028910B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3480654A (en) * | 1965-03-12 | 1969-11-25 | Goldschmidt Ag Th | Process for preparing organo-tin, -boron, -aluminum, -silicon, -phosphorous,-zinc and -mercury compounds |
| WO1993010124A1 (en) * | 1991-11-19 | 1993-05-27 | Air Products And Chemicals, Inc. | Process for the preparation of di-alkyl compounds of group 2b metals |
| TW200745144A (en) * | 2006-04-24 | 2007-12-16 | Ube Industries | High purity diisopropyl zinc and its method for manufacture |
| CN104774214A (en) * | 2015-04-28 | 2015-07-15 | 河南承明光电新材料股份有限公司 | Preparation method for dimethylzinc |
| CN105669722A (en) * | 2016-03-02 | 2016-06-15 | 南京大学 | Method for preparing high-purity dimethylzine by utilizing prepared trimethyl gallium by-product |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112028910A (en) | 2020-12-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103733416A (en) | Method for producing lithium tetrafluoroborate solution | |
| CN101870711B (en) | Synthesis method of tris(trimethylsilyl) phosphate | |
| CN102659090A (en) | Preparation method of lithium hexafluorophate | |
| CN102020669B (en) | Method for industrially preparing trimethyl gallium | |
| CN104744500B (en) | The purification process of the trialkyl compound of liquid state III family metal | |
| CN112028910B (en) | Preparation method of high-purity dimethyl zinc | |
| CN112028921B (en) | Preparation method of high-purity trimethylaluminum | |
| CN114149401A (en) | Synthesis method of vinyl ethylene carbonate | |
| CN101857270A (en) | Method for synthesizing high-purity arsine | |
| CN103965227A (en) | Industrial purification method of trimethyl gallium | |
| CN113583051B (en) | Method for preparing high-purity trimethylantimony by using trimethylaluminum and antimony trichloride | |
| CN112110950A (en) | Preparation method of disilane | |
| CN113831367B (en) | Purification method for removing diethyl ether from trimethyl antimony | |
| CN112028920B (en) | Method for synthesizing high-purity trimethylaluminum by using nonpolar solvent | |
| CN113801164A (en) | Preparation method of trimethyl bismuth | |
| CN102225946A (en) | Method for preparing high purity alkoxysilanes from polysilicon byproduct silicon tetrachloride | |
| CN113072573B (en) | Method for preparing chelated boron-based lithium salt by recycling electrolyte from waste lithium ion battery | |
| CN106565573B (en) | The preparation method of two (dimethylamino) telluriums | |
| CN109503653B (en) | Synthesis method of tri (trihydrocarbylsilyl) phosphate | |
| CN113060718A (en) | Method for preparing lithium difluorophosphate by recycling electrolyte from waste lithium ion battery | |
| CN110922306B (en) | Synthesis process of 2, 3-difluoro-4-alkoxyl phenol | |
| CN111484515B (en) | Synthesis method of s-triazine pinacol borate | |
| CN104774214B (en) | A kind of preparation method of zinc methide | |
| CN110372520B (en) | Catalytic synthesis method of p-n-butylaniline | |
| CN115521210B (en) | Perovskite material and preparation method and application thereof |
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 | ||
| CP03 | Change of name, title or address |
Address after: No. 88 Baoshun Road, Economic and Technological Development Zone, Wuhu City, Anhui Province, 241000 Patentee after: Anhui Yagesheng Electronic New Materials Co.,Ltd. Address before: 241000 No.26 chizhushan Road, economic and Technological Development Zone, Wuhu City, Anhui Province Patentee before: ANHUI ARGOSUN NEW ELECRONIC MATERIALS Co.,Ltd. |
|
| CP03 | Change of name, title or address |