CN116574126B - Synthesis method of high-purity tin tert-butoxide - Google Patents
Synthesis method of high-purity tin tert-butoxide Download PDFInfo
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- CN116574126B CN116574126B CN202310826938.8A CN202310826938A CN116574126B CN 116574126 B CN116574126 B CN 116574126B CN 202310826938 A CN202310826938 A CN 202310826938A CN 116574126 B CN116574126 B CN 116574126B
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- OSXGKVOYAKRLCS-UHFFFAOYSA-N 2-methylpropan-2-olate;tin(4+) Chemical compound CC(C)(C)O[Sn](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C OSXGKVOYAKRLCS-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000001308 synthesis method Methods 0.000 title claims description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- 238000001816 cooling Methods 0.000 claims abstract description 27
- 238000003756 stirring Methods 0.000 claims abstract description 24
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000010992 reflux Methods 0.000 claims abstract description 16
- 239000012467 final product Substances 0.000 claims abstract description 12
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 11
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims abstract description 11
- 239000000706 filtrate Substances 0.000 claims abstract description 10
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 238000004821 distillation Methods 0.000 claims abstract description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 20
- 230000035484 reaction time Effects 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 11
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract description 6
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052744 lithium Inorganic materials 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 238000004255 ion exchange chromatography Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical group [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical group 0.000 description 1
- 125000001979 organolithium group Chemical group 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2224—Compounds having one or more tin-oxygen linkages
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2296—Purification, stabilisation, isolation
-
- 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
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention discloses a method for synthesizing high-purity tin tert-butoxide, and particularly relates to the technical field of organic synthesis. Adding an organic lithium reagent and an organic solvent into a reaction container, controlling the reaction temperature, introducing dimethylamine gas, and recovering the room temperature to stir for reaction; cooling, dropwise adding tin tetrachloride, and recovering room temperature after the dropwise addition is finished, and stirring and reacting; continuously cooling, dropwise adding tertiary butanol, and carrying out reflux reaction after the dropwise adding is finished; after the reflux reaction is finished, cooling to room temperature, filtering, and carrying out reduced pressure distillation on the filtrate to obtain the final product of the high-purity tin tert-butoxide. The preparation method of the invention has the advantages that firstly, the yield of the tin tert-butoxide can be greatly improved; secondly, chloride ions in the tin tert-butoxide final product can be reduced to below 1 ppm; thirdly, the use amount of diethylamine is greatly reduced.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing high-purity tin tert-butoxide.
Background
Tin tert-butoxide is mainly prepared by adding diethylamine as an acid-binding agent into alkane solvent, such as PCT patent WO 2021038523A 1, wherein the byproduct is diethylamine hydrochloride.
The method has the advantages that the reaction is simpler, the product can be obtained in one step, but the defects are that the yield is low, the consumption of diethylamine is large (more than 8 equivalents), and a lot of diethylamine hydrochloride can remain in the product, so that chloride ions exceed the standard, and the purity of the product is seriously influenced.
Disclosure of Invention
Therefore, the invention provides a method for synthesizing high-purity tin tert-butoxide, which aims to solve the problem of low purity of the existing synthesized tin tert-butoxide.
In order to achieve the above object, the present invention provides the following technical solutions:
the synthesis method of the high-purity tin tert-butoxide provided by the invention comprises the following steps:
adding an organic lithium reagent and an organic solvent into a reaction container, controlling the reaction temperature, introducing dimethylamine gas, and recovering the room temperature to stir for reaction;
step two, cooling, dropwise adding tin tetrachloride, and recovering room temperature after the dropwise adding is finished, and stirring and reacting;
step three, cooling, dropwise adding tertiary butanol, and carrying out reflux reaction after the dropwise adding is finished;
and step four, after the reflux reaction is finished, cooling to room temperature, filtering, and distilling the filtrate under reduced pressure to obtain the final product of high-purity tin tert-butoxide.
Further, in the first step, the organolithium reagent is an organic compound containing a lithium element; examples include, but are not limited to, n-butyllithium or t-butyllithium.
Further, in the first step, the organic solvent is an organic reagent commonly used as a solvent; examples include, but are not limited to, n-hexane, n-heptane, toluene, diethyl ether, methylene chloride, and the like.
Further, in the first step, the reaction temperature is controlled to be-20-10 ℃.
Further, in the first step, the stirring reaction time is 6-24 hours.
Further, in the second step, the temperature is reduced to 0-15 ℃.
Further, in the second step, the stirring reaction time is 4-12 hours.
Further, in the third step, the temperature is reduced to 0-15 ℃.
Further, in the third step, the reflux reaction time is 6-24 hours.
Further, in the fourth step, the reduced pressure distillation condition is 40-60Pa,60-80 ℃.
The invention has the following advantages:
the preparation method of the invention has the advantages that firstly, the yield of the tin tert-butoxide can be greatly improved; secondly, chloride ions in the tin tert-butoxide final product can be reduced to below 1 ppm; thirdly, the use amount of diethylamine is greatly reduced.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below. It will be apparent to those of ordinary skill in the art that the drawings in the following description are exemplary only and that other implementations can be obtained from the extensions of the drawings provided without inventive effort.
The structures, proportions, sizes, etc. shown in the present specification are shown only for the purposes of illustration and description, and are not intended to limit the scope of the invention, which is defined by the claims, so that any structural modifications, changes in proportions, or adjustments of sizes, which do not affect the efficacy or the achievement of the present invention, should fall within the ambit of the technical disclosure.
FIG. 1 is a hydrogen spectrum of tin tert-butoxide according to example 1 of the present invention.
Detailed Description
Other advantages and advantages of the present invention will become apparent to those skilled in the art from the following detailed description, which, by way of illustration, is to be read in connection with certain specific embodiments, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Adding an organic lithium reagent (including but not limited to n-butyllithium and tert-butyllithium) and an organic solvent (including but not limited to n-hexane, n-heptane, toluene, diethyl ether, dichloromethane and the like) into a four-mouth bottle under the protection of nitrogen, controlling the temperature to be-20-10 ℃, introducing dimethylamine gas, and recovering the room temperature and stirring for 6-24 hours.
Cooling to 0-15 ℃, dropwise adding tin tetrachloride, and after the dropwise adding, returning to room temperature and stirring for 4-12 hours.
Cooling to 0-15 ℃, dropwise adding tertiary butanol, refluxing for 6-24 hours after the dropwise adding is finished, cooling to room temperature after the reaction is finished, filtering, and carrying out reduced pressure distillation (40-60 Pa,60-80 ℃) on the filtrate to obtain a final product, wherein the yield is as high as more than 90%.
The content of chloride ions detected by ion chromatography is less than 1ppm.
Example 1
1L of n-hexane solution (2.5M) of n-butyllithium was added under nitrogen protection to a 5L four-necked flask, the temperature was controlled at 0℃and 113g (2.5 mol) of dimethylamine gas was introduced thereinto, followed by stirring at room temperature for 6 hours.
Cooling to 0 ℃, dropwise adding 162g (0.62 mol) of stannic chloride, and stirring for 12 hours at room temperature after the completion of dropwise adding.
Cooling to 0 ℃, dropwise adding 231g (3.1 mol) of tertiary butanol, refluxing for 12 hours after the dropwise adding is finished, cooling to room temperature after the reaction is finished, filtering, and distilling filtrate under reduced pressure (40-60 Pa,60-70 ℃) to obtain 237g (0.58 mol) of a final product, wherein the yield is 93%; the hydrogen spectrum is shown in FIG. 1. The content of chloride ions was 0.3ppm by ion chromatography.
Comparative example 1
In a 5L four-necked flask, 1L of n-hexane solution (2.5M) of n-butyllithium was added under nitrogen protection, and 113g (2.5 mol) of dimethylamine gas was introduced at room temperature, followed by stirring at room temperature for 6 hours.
Cooling to 0 ℃, dropwise adding 162g (0.62 mol) of stannic chloride, and stirring for 12 hours at room temperature after the completion of dropwise adding.
Cooling to 0 ℃, dropwise adding 231g (3.1 mol) of tertiary butanol, refluxing for 12 hours after the dropwise adding is finished, cooling to room temperature after the reaction is finished, filtering, and distilling filtrate under reduced pressure (40-60 Pa,60-70 ℃) to obtain 214g (0.52 mol) of a final product, wherein the yield is 84%. The content of chloride ions was 0.8ppm by ion chromatography.
In contrast to example 1, dimethylamine gas was introduced at room temperature, and the reaction yield was reduced.
Comparative example 2
1L of n-hexane solution (2.5M) of n-butyllithium was added under nitrogen protection to a 5L four-necked flask, the temperature was controlled at 0℃and 113g (2.5 mol) of dimethylamine gas was introduced thereinto, followed by stirring at room temperature for 6 hours.
162g (0.62 mol) of tin tetrachloride was added dropwise at room temperature, and the mixture was stirred at room temperature for 12 hours after completion of the dropwise addition.
Cooling to 0 ℃, dropwise adding 231g (3.1 mol) of tertiary butanol, refluxing for 12 hours after the dropwise adding is finished, cooling to room temperature after the reaction is finished, filtering, and distilling the filtrate under reduced pressure (40-60 Pa,60-70 ℃) to obtain 176g (0.43 mol) of a final product, wherein the yield is 69%. The content of chloride ions was 8.6ppm by ion chromatography.
In contrast to example 1, tin tetrachloride was added dropwise at room temperature, and the reaction yield was lowered.
Comparative example 3
1L of n-hexane solution (2.5M) of n-butyllithium was added under nitrogen protection to a 5L four-necked flask, the temperature was controlled at 0℃and 113g (2.5 mol) of dimethylamine gas was introduced thereinto, followed by stirring at room temperature for 6 hours.
Cooling to 0 ℃, dropwise adding 162g (0.62 mol) of stannic chloride, and stirring for 12 hours at room temperature after the completion of dropwise adding.
231g (3.1 mol) of t-butanol was added dropwise at room temperature, the reflux reaction was completed at room temperature for 12 hours, the reaction was cooled to room temperature and filtered, and the filtrate was distilled under reduced pressure (40-60 Pa,60-70 ℃ C.) to give 82g (0.20 mol) of the final product in 32% yield. The content of chloride ions was measured by ion chromatography to be 13.8ppm.
In contrast to example 1, the reaction was carried out at room temperature for 12 hours without refluxing, and the reaction yield was lowered.
Comparative example 4
In a 5L four-necked flask, 1L of n-hexane solution (2.5M) of n-butyllithium was added under nitrogen protection, the temperature was controlled at 0℃and 182g (2.5 mol) of dimethylamine was added thereto, followed by stirring at room temperature for 1 hour.
Cooling to 0 ℃, dropwise adding 162g (0.62 mol) of stannic chloride, and stirring for 12 hours at room temperature after the completion of dropwise adding.
Cooling to 0 ℃, dropwise adding 231g (3.1 mol) of tertiary butanol, refluxing for 12 hours after the dropwise adding is finished, cooling to room temperature after the reaction is finished, filtering, and distilling filtrate under reduced pressure (40-60 Pa,60-70 ℃) to obtain 186g (0.45 mol) of a final product, wherein the yield is 73%. The content of chloride ions was 5.2ppm by ion chromatography.
In contrast to example 1, the stirring time of n-butyllithium and dimethylamine was shortened, and the reaction yield was reduced.
Comparative example 5
Under the protection of nitrogen in a 5L four-necked flask, 1L of n-hexane solution (2.5M) of n-butyllithium was added thereto, the temperature was controlled at 0℃and 113g (2.5 mol) of diethylamine was introduced thereinto, followed by stirring at room temperature for 6 hours.
Cooling to 0 ℃, dropwise adding 162g (0.62 mol) of stannic chloride, and stirring for 12 hours at room temperature after the completion of dropwise adding.
Cooling to 0 ℃, dropwise adding 231g (3.1 mol) of tertiary butanol, refluxing for 12 hours after the dropwise adding is finished, cooling to room temperature after the reaction is finished, filtering, and distilling filtrate under reduced pressure (40-60 Pa,60-70 ℃) to obtain 230g (0.56 mol) of a final product, wherein the yield is 90%. The content of chloride ions was 1.5ppm by ion chromatography.
In comparison with example 1, the acid binding agent of the comparative example uses diethylamine, and the reaction yields are not much different; however, the chloride ion content in the comparative example was 1.5ppm, which is significantly higher than that of the present invention.
While the invention has been described in detail in the foregoing general description and specific examples, it will be apparent to those skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.
Claims (8)
1. The synthesis method of the high-purity tin tert-butoxide is characterized by comprising the following steps of:
adding n-butyllithium and an organic solvent into a reaction container, controlling the reaction temperature, introducing dimethylamine gas, and recovering the room temperature to stir for reaction;
step two, cooling, dropwise adding tin tetrachloride, and recovering room temperature after the dropwise adding is finished, and stirring and reacting;
step three, cooling, dropwise adding tertiary butanol, and carrying out reflux reaction after the dropwise adding is finished;
and step four, after the reflux reaction is finished, cooling to room temperature, filtering, and distilling the filtrate under reduced pressure to obtain the final product of high-purity tin tert-butoxide.
2. The method for synthesizing high-purity tin tert-butoxide according to claim 1, wherein in the first step, the reaction temperature is controlled to be-20-10 ℃.
3. The method for synthesizing high-purity tin tert-butoxide according to claim 1, wherein in the first step, the stirring reaction time is 6 to 24 hours.
4. The method for synthesizing high-purity tin tert-butoxide according to claim 1, wherein in the second step, the temperature is reduced to 0-15 ℃.
5. The method for synthesizing high-purity tin tert-butoxide according to claim 1, wherein in the second step, the stirring reaction time is 4-12 hours.
6. The method for synthesizing high-purity tin tert-butoxide according to claim 1, wherein in the third step, the temperature is reduced to 0-15 ℃.
7. The method for synthesizing high-purity tin tert-butoxide according to claim 1, wherein in the third step, the reflux reaction time is 6 to 24 hours.
8. The method for synthesizing high-purity tin tert-butoxide according to claim 1, wherein in the fourth step, the reduced pressure distillation condition is 40-60pa,60-80 ℃.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202310826938.8A CN116574126B (en) | 2023-07-07 | 2023-07-07 | Synthesis method of high-purity tin tert-butoxide |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202310826938.8A CN116574126B (en) | 2023-07-07 | 2023-07-07 | Synthesis method of high-purity tin tert-butoxide |
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| CN116574126A CN116574126A (en) | 2023-08-11 |
| CN116574126B true CN116574126B (en) | 2023-09-22 |
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3794670A (en) * | 1971-06-30 | 1974-02-26 | Procter & Gamble | Preparation of organotin compounds |
| US3946056A (en) * | 1974-07-26 | 1976-03-23 | Owens-Illinois, Inc. | Method for producing stannic tertiary alkoxide |
| JPS61205289A (en) * | 1985-03-08 | 1986-09-11 | Mitsubishi Metal Corp | Production of tin alkoxide |
| US4731461A (en) * | 1986-06-09 | 1988-03-15 | Stauffer Chemical Company | Process for preparing tin alkoxides |
| JPH07258277A (en) * | 1994-03-25 | 1995-10-09 | Kooriyama Kasei Kk | Method for removing halogen from tin(iv)-tetraalkoxide |
| KR20110025082A (en) * | 2009-09-02 | 2011-03-09 | 주식회사 엘지화학 | Organotin compounds |
| CN109988189A (en) * | 2019-05-09 | 2019-07-09 | 苏州复纳电子科技有限公司 | A kind of synthetic method of four (the first and second amidos) tin |
| CN114630834A (en) * | 2019-08-29 | 2022-06-14 | 海星化学有限公司 | Organometallic compounds for depositing high purity tin oxide and dry etching of said tin oxide films and deposition reactors |
-
2023
- 2023-07-07 CN CN202310826938.8A patent/CN116574126B/en active Active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3794670A (en) * | 1971-06-30 | 1974-02-26 | Procter & Gamble | Preparation of organotin compounds |
| US3946056A (en) * | 1974-07-26 | 1976-03-23 | Owens-Illinois, Inc. | Method for producing stannic tertiary alkoxide |
| JPS61205289A (en) * | 1985-03-08 | 1986-09-11 | Mitsubishi Metal Corp | Production of tin alkoxide |
| US4731461A (en) * | 1986-06-09 | 1988-03-15 | Stauffer Chemical Company | Process for preparing tin alkoxides |
| JPH07258277A (en) * | 1994-03-25 | 1995-10-09 | Kooriyama Kasei Kk | Method for removing halogen from tin(iv)-tetraalkoxide |
| KR20110025082A (en) * | 2009-09-02 | 2011-03-09 | 주식회사 엘지화학 | Organotin compounds |
| CN109988189A (en) * | 2019-05-09 | 2019-07-09 | 苏州复纳电子科技有限公司 | A kind of synthetic method of four (the first and second amidos) tin |
| CN114630834A (en) * | 2019-08-29 | 2022-06-14 | 海星化学有限公司 | Organometallic compounds for depositing high purity tin oxide and dry etching of said tin oxide films and deposition reactors |
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| CN116574126A (en) | 2023-08-11 |
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Address after: Cg05-223, building 8, yard 1, Zhongguancun East Road, Haidian District, Beijing 100086 Patentee after: Yanfeng Technology (Beijing) Co.,Ltd. Address before: Cg05-223, building 8, yard 1, Zhongguancun East Road, Haidian District, Beijing 100086 Patentee before: Yanfeng Technology (Beijing) Co.,Ltd. |