CN112028910A - Preparation method of high-purity dimethyl zinc - Google Patents
Preparation method of high-purity dimethyl zinc Download PDFInfo
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- CN112028910A CN112028910A CN202010794418.XA CN202010794418A CN112028910A CN 112028910 A CN112028910 A CN 112028910A CN 202010794418 A CN202010794418 A CN 202010794418A CN 112028910 A CN112028910 A CN 112028910A
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- zinc
- organic solvent
- prepare
- dimethyl zinc
- solution
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- AXAZMDOAUQTMOW-UHFFFAOYSA-N dimethylzinc Chemical compound C[Zn]C AXAZMDOAUQTMOW-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 26
- 239000003960 organic solvent Substances 0.000 claims abstract description 14
- 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
- 239000011592 zinc chloride Substances 0.000 claims abstract description 13
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 13
- 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 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
- 239000007788 liquid Substances 0.000 claims abstract description 7
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 3
- 239000001103 potassium chloride Substances 0.000 claims abstract description 3
- 235000011164 potassium chloride Nutrition 0.000 claims abstract description 3
- 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
- 238000003756 stirring Methods 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- UGDAWAQEKLURQI-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;hydrate Chemical compound O.OCCOCCO UGDAWAQEKLURQI-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 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 8
- -1 zinc halide Chemical class 0.000 abstract description 11
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 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
- 238000009616 inductively coupled plasma Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000004065 semiconductor Substances 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
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 2
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 2
- 230000005311 nuclear magnetism Effects 0.000 description 2
- 239000000126 substance Substances 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
- 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
- 230000002708 enhancing effect Effects 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000002243 precursor Substances 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
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- 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 halogenated methane solution into a mixture of the magnesium chips and the organic solvent under the anhydrous and oxygen-free conditions to prepare a Grignard reagent; 2. dissolving zinc chloride by using an organic solvent to prepare a zinc chloride solution; 3. dropwise adding a potassium chloride solution into the Grignard reagent, heating and refluxing for 12h, and reacting to prepare a dimethyl zinc solution; 4. cooling after the reflux is finished, replacing a normal pressure distillation device, cooling a receiving device by using liquid nitrogen, and controlling the temperature to be 150-160 ℃ to receive the product; 5. sampling and analyzing, and performing nuclear magnetic detection and Icp detection on the product. The excessive Grignard reagent and the metal zinc halide are adopted to react to prepare the alkyl zinc, the cost is low, the reaction efficiency is poor, the safety is high, organic impurities are not easy to introduce, 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, and among them, gallium nitride materials are widely used in high power optoelectronic devices by virtue of their wide direct band gap and high thermal conductivity. The zinc oxide is a new generation of short wavelength semiconductor photoelectric material after gallium nitride, and the zinc oxide wide band gap semiconductor material has wide application prospect and great application prospect in the fields of sensors, batteries, ultraviolet photoelectric detection, lasers and the like. 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 the demand of the high-purity dimethyl zinc in the integrated circuit industry is gradually increased. There are two schemes for the preparation of dimethylzinc: firstly, the diethyl zinc is added after the trimethyl aluminum reacts with the zinc chloride, the raw materials of the scheme are expensive, and the product contains more trimethyl aluminum and diethyl zinc organic impurities and is difficult to purify; and secondly, dimethyl zinc is generated by adding diethyl zinc into dimethyl aluminum chloride serving as a raw material under a heating condition, and colorless and transparent dimethyl zinc is obtained through normal-pressure rectification separation, but the dimethyl aluminum chloride is a byproduct for preparing trimethyl gallium, the raw material is not easy to obtain, and gallium pollution is caused, so that the preparation of the dimethyl zinc is limited, and 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 to react with metal zinc halide to prepare alkyl zinc and solves the problems of high price of raw materials and harsh preparation conditions of the high-purity dimethyl zinc preparation.
The invention provides a preparation method of high-purity dimethyl zinc, which comprises the following steps: 1. adding a halogenated methane solution into a mixture of the magnesium chips and the organic solvent under the anhydrous and oxygen-free conditions to prepare a Grignard reagent; 2. dissolving zinc chloride by using an organic solvent to prepare a zinc chloride solution; 3. dropwise adding a potassium chloride solution into the Grignard reagent, heating and refluxing for 12h, and reacting to prepare a dimethyl zinc solution; 4. cooling after the reflux is finished, replacing a normal pressure distillation device, cooling a receiving device by using liquid nitrogen, and controlling the temperature to be 150-160 ℃ to receive the product; 5. sampling and analyzing, and performing nuclear magnetic detection and Icp detection on the product.
The further improvement lies in that: in the step 1 and the step 2, the organic solvent is one of n-butyl ether and diethylene glycol dimethyl ether, water and impurity removal treatment is carried out before the organic solvent is used, anhydrous calcium chloride is added into the organic solvent, stirring is carried out for 2 hours, and the organic solvent is used after filtration.
The further improvement lies in that: and (3) before the magnesium chips are used in the step (1), drying and dewatering the magnesium chips, heating the magnesium chips to 100 ℃, and vacuumizing the magnesium chips for 2 hours under the absolute pressure.
The further improvement lies in that: in the step 1, methyl iodide is used as the monohalogenated methane, and a molecular sieve is added before the monohalogenated methane is used for removing water, and the monohalogenated methane is used after being filtered.
The further improvement lies in that: and (3) adding thionyl chloride before the zinc chloride is used in the step (2), heating and refluxing for 2h, and then heating and sucking the thionyl chloride under absolute pressure.
The invention has the beneficial effects that: the zinc alkyl is prepared by reacting excessive Grignard reagent with metal zinc halide, so that the cost is low, the reaction efficiency is poor, the safety is high, organic impurities are not easy to introduce, harsh reaction conditions are not required for synthesis, the raw materials are cheap, and the operation is simple.
Detailed Description
For the purpose of enhancing understanding of the present invention, the present invention will be further described in detail with reference to the following examples, which are provided for illustration only and are not to be construed as limiting the scope of the present invention. Example one
The embodiment provides a preparation method of high-purity dimethyl zinc, which comprises the following steps:
1. adding 2.75mol of magnesium chips and 1000ml of n-butyl ether into a 2L two-mouth bottle, building a normal-pressure reflux device, and starting stirring; dropwise adding 2.5mol of methyl iodide into the two-mouth bottle, rapidly raising the temperature of the bottom bottle with a small amount of reflux, and keeping stirring for 1h after the methyl iodide is dropwise added to obtain a Grignard reagent: methyl magnesium iodide n-butyl ether solution;
2. dissolving 1.2mol of zinc chloride in 400ml of n-butyl ether to prepare a zinc chloride n-butyl ether solution, slowly dropwise adding the zinc chloride n-butyl ether solution into the methyl magnesium iodide n-butyl ether solution obtained in the step 1, simultaneously carrying out rapid stirring, controlling the temperature to be 60 ℃, keeping the temperature of 60 ℃ for refluxing for 12 hours after the dropwise adding is finished, and finishing the reaction;
3. and (3) building an atmospheric distillation device, ensuring good air tightness, carrying out atmospheric distillation, controlling the temperature of a bottom bottle to be 150-160 ℃, controlling the condensation temperature to be-20 ℃ to-10 ℃, controlling the temperature of a liquid nitrogen receiving device to be-60 ℃ to-50 ℃, distilling to obtain a colorless transparent liquid, weighing 97.1g, and detecting nuclear magnetism and ICP of the product.
The yield of the substances in the scheme is 85%, wherein the n-butyl ether can be recycled, and the product is detected by a JNM-ECZ400S nuclear magnetic resonance spectrometer: 1HNMR (400MHz, C6D 6): -0.67(s,6H), no impurity peaks; the inductively coupled plasma emission spectrometer (Optima8000) detects that the inorganic element is less than 1ppm, and the purity reaches 6N.
Example two
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-mouth bottle, building a normal-pressure reflux device, and starting stirring; and (3.75 mol) of methyl iodide is dropwise added into the two bottles, the temperature of the bottom bottle is rapidly increased with a small amount of reflux, and stirring is kept for 1h after the methyl iodide is dropwise added, so that a Grignard reagent is obtained: methyl magnesium iodide diethylene glycol dimethyl ether solution;
2. dissolving 1.8mol of zinc chloride in 600ml of diethylene glycol dimethyl ether to prepare a zinc chloride diethylene glycol dimethyl ether solution, slowly dropwise adding the zinc chloride diethylene glycol dimethyl ether solution into the methyl magnesium iodide diethylene glycol dimethyl ether solution obtained in the step 1, simultaneously carrying out rapid stirring, controlling the temperature to be 60 ℃, keeping 60 ℃ for refluxing for 12 hours after dropwise adding is finished, and finishing the reaction;
3. and (3) building an atmospheric distillation device, ensuring good air tightness, carrying out atmospheric distillation, controlling the temperature of a bottom bottle to be 150-160 ℃, controlling the condensation temperature to be-20 ℃ to-10 ℃, controlling the temperature of a liquid nitrogen receiving device to be-60 ℃ to-50 ℃, distilling to obtain a colorless transparent liquid, weighing 149.5g, and detecting nuclear magnetism and ICP of the product.
The yield of the substance in the scheme is 87%, wherein the diethylene glycol dimethyl ether can be recycled, and the product is detected by a JNM-ECZ400S nuclear magnetic resonance spectrometer: 1HNMR (400MHz, C6D 6): 0.67(s,6H), no impurity peak; the inductively coupled plasma emission spectrometer (Optima8000) detects that the inorganic element is less than 1ppm, and the purity reaches 6N.
The Grignard reagent preparation reaction formula is:
the reaction equation for preparing the dimethyl zinc is as follows:
the excessive Grignard reagent and the metal zinc halide are adopted to react to prepare the alkyl zinc, the cost is low, the reaction efficiency is poor, the safety is high, organic impurities are not easy to introduce, the synthesis does not need harsh reaction conditions, the raw materials are cheap, and the operation is simple.
Claims (5)
1. The preparation method of the high-purity dimethyl zinc is characterized by comprising the following steps: (1) adding a halogenated methane solution into a mixture of the magnesium chips and the organic solvent under the anhydrous and oxygen-free conditions to prepare a Grignard reagent; (2) dissolving zinc chloride by using an organic solvent to prepare a zinc chloride solution; (3) dropwise adding a potassium chloride solution into the Grignard reagent, heating and refluxing for 12h, and reacting to prepare a dimethyl zinc solution; (4) cooling after the reflux is finished, replacing a normal pressure distillation device, cooling a receiving device by using liquid nitrogen, and controlling the temperature to be 150-160 ℃ to receive the product; (5) and sampling and analyzing, and performing nuclear magnetic detection and Icp detection on the product.
2. The method for preparing high-purity dimethyl zinc according to claim 1, wherein the method comprises the following steps: in the step 1 and the step 2, the organic solvent is one of n-butyl ether and diethylene glycol dimethyl ether, water and impurity removal treatment is carried out before the organic solvent is used, anhydrous calcium chloride is added into the organic solvent, stirring is carried out for 2 hours, and the organic solvent is used after filtration.
3. The method for preparing high-purity dimethyl zinc according to claim 1, wherein the method comprises the following steps: and (3) before the magnesium chips are used in the step (1), drying and dewatering the magnesium chips, heating the magnesium chips to 100 ℃, and vacuumizing the magnesium chips for 2 hours under the absolute pressure.
4. The method for preparing high-purity dimethyl zinc according to claim 1, wherein the method comprises the following steps: in the step 1, methyl iodide is used as the monohalogenated methane, and a molecular sieve is added before the monohalogenated methane is used for removing water, and the monohalogenated methane is used after being filtered.
5. The method for preparing high-purity dimethyl zinc according to claim 1, wherein the method comprises the following steps: and (3) adding thionyl chloride before the zinc chloride is used in the step (2), heating and refluxing for 2h, and then heating and sucking the thionyl chloride under absolute pressure.
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 |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202010794418.XA CN112028910B (en) | 2020-08-10 | 2020-08-10 | Preparation method of high-purity dimethyl zinc |
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| CN112028910B CN112028910B (en) | 2023-06-30 |
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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 |
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| CN112028910B (en) | 2023-06-30 |
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