CN118005670A - Preparation method of 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undecan-1-yl) oxy) ethane - Google Patents
Preparation method of 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undecan-1-yl) oxy) ethane Download PDFInfo
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- CN118005670A CN118005670A CN202311827614.2A CN202311827614A CN118005670A CN 118005670 A CN118005670 A CN 118005670A CN 202311827614 A CN202311827614 A CN 202311827614A CN 118005670 A CN118005670 A CN 118005670A
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- -1 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undecan-1-yl) oxy) ethane Chemical compound 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 55
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 19
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 13
- 239000010703 silicon Substances 0.000 claims abstract description 13
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 8
- 239000000706 filtrate Substances 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 238000004821 distillation Methods 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims description 4
- 235000012239 silicon dioxide Nutrition 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 8
- 239000002808 molecular sieve Substances 0.000 abstract description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 abstract description 5
- 238000010992 reflux Methods 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 abstract 1
- 239000012265 solid product Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to a preparation method of 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silicon bicyclo [3.3.3] undecane-1-yl) oxy) ethane, which comprises the following steps: glycol, a silicon source, triethanolamine and a catalyst are sequentially added into a reaction bottle, and the reaction bottle is heated for reaction after nitrogen replacement. Filtering after the reaction is finished, removing glycol by reduced pressure distillation after the filtrate is replaced by nitrogen, adding an organic solvent into the residue, stirring, filtering, washing and drying to obtain the nitrogen-containing organosilicon compound. The synthesis method of the invention adopts silicon source, glycol and triethanolamine to react under the action of catalyst to prepare the nitrogenous organosilicon compound, and the product is purer. The reaction utilizes molecular sieve to reflux and dehydrate, and glycol is boiled and reflowed to pass through the molecular sieve to take away the water generated in the reaction, so as to promote the reaction.
Description
Technical Field
The invention relates to the field of organosilicon synthesis, in particular to synthesis of nitrogen-containing organosilicon compounds.
Background
There have been studies reporting the synthesis of 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane, a nitrogenous organosilicon compound (Voronkov, m.g. et al 1975,11 (6), 656-658), using the reaction of 1-hydroxysilicon tricyclic and 1-ethoxysilatricyclic with alkanediols to give the target product. Excess diol and dried sodium alkoxide are used in the reaction while gradually increasing the temperature to boiling point to facilitate the reaction. After the reaction was completed, the mixture was cooled and filtered to isolate a product. However, this approach has several drawbacks and limitations: unstable byproducts are generated in the reaction, and the target product is difficult to purify; the synthesis process is complex, and the raw material cost is high; h 2 is generated in the reaction process, and certain potential safety hazard exists.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to invent a preparation method of a nitrogen-containing organosilicon compound in a short flow, namely, a silicon source reacts with alcohol and triethanolamine under the action of a catalyst to directly synthesize the nitrogen-containing organosilicon compound.
The specific implementation method of the invention is as follows: glycol, a silicon source, triethanolamine and a catalyst are sequentially added into a reaction bottle, and the reaction bottle is heated for reaction after nitrogen replacement. Filtering after the reaction is finished, removing glycol by vacuum distillation after the filtrate is replaced by nitrogen, adding an organic solvent into the residue, stirring, filtering, washing and drying to obtain a nitrogenous organosilicon compound, specifically 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane.
The silicon source is one or more of white carbon black and silicic acid by precipitation method.
The diol is ethylene glycol.
The catalyst is one or more of imidazole and 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU).
The molar ratio of the silicon source to the catalyst is 1:0.5-1.0.
The mol ratio of the silicon source to the triethanolamine is 1:1.1-2.
The heating reaction temperature is 200-220 ℃.
The organic solvent is one or more of methanol, ethanol and tetrahydrofuran.
The molecular formula of the nitrogen-containing organosilicon compound is as follows: c 14H28O8N2Si2; the Chinese name is: 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane; the molecular structural formula is shown in figure 1.
The synthesis method of the invention adopts silicon source, glycol and triethanolamine to react under the action of catalyst to prepare the nitrogenous organosilicon compound, and the product is purer. The reaction utilizes molecular sieve to reflux and dehydrate, and glycol is boiled and reflowed to pass through the molecular sieve to take away the water generated in the reaction, so as to promote the reaction.
The invention has the beneficial effects that: 1. the invention avoids the intermediate products which are difficult to separate and purify, can greatly reduce the energy consumption, reduces byproducts and is environment-friendly; 2. the nitrogenous organosilicon compound synthesized by the preparation method has short flow and good atom economy; 3. the method has higher yield and expandability and practicability.
Drawings
FIG. 1 is a molecular structural formula of 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane of the present invention.
FIG. 2 is an infrared spectrum of 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane prepared in example 1.
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane prepared in example 1.
FIG. 4 is a high resolution mass spectrum of 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane prepared in example 1.
FIG. 5 IR spectra of tetramethyl silicate and analytically pure tetramethyl silicate obtained in example 6.
Detailed Description
The present invention will be described in further detail below in order to enable those skilled in the art to better understand the technical scheme of the present invention.
Example 1
To the dried two-necked flask were added 78.29g of ethylene glycol, 4.01g of precipitated silica, 12.08g of triethanolamine and 3.64g of imidazole, and after nitrogen substitution, the mixture was reacted at 200℃for 12 hours, and the ethylene glycol was distilled off under reduced pressure at 160 ℃. Cooling to 50 ℃, adding ethanol into the residue for dissolution, stirring for 12 hours, centrifuging, washing with ethanol twice, and drying to obtain 8.61g of solid product, wherein the yield is 63.15%.
The infrared spectrum of the solid product is shown in figure 3. 1456cm -1 is a bending vibration peak of methylene, 2913cm -1 is an asymmetric stretching vibration peak of methylene, 2883cm -1 is a symmetric stretching vibration peak of methylene, 1047cm -1 is a stretching vibration peak of C-O, 1079cm -1 and 870cm -1 are stretching vibration peaks of Si-O-C, 1275cm -1 is a stretching vibration peak of C-N.
The nuclear magnetic resonance hydrogen spectrum of the solid product is shown in FIG. 4, and the multiple peaks at chemical shift of 2.6ppm correspond to hydrogen numbered 6,10,13,18,22,25 on the structural formula, the single peak at chemical shift of 3.50ppm corresponds to hydrogen numbered 1,2 on the structural formula, and the multiple peaks at chemical shift of 3.54ppm correspond to hydrogen numbered 7,9,12,19,21,24 on the structural formula. As a result of the combination of FTIR and 1 H-NMR analysis, the product was 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane, which was a nitrogen-containing organosilicon compound [N(CH2CH2O)3SiOCH2CH2OSi(OCH2CH2)3N].
The high resolution mass spectrum of the solid product is shown in fig. 5, the molecular weight of the solid product is 408.14 (hydrogenation 409.14, sodium addition 431.14). Combining the results of FTIR, 1 H-NMR and HRMS analysis, it was essentially determined that the product was the nitrogen-containing organosilicon compound 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane [N(CH2CH2O)3SiOCH2CH2OSi(OCH2CH2)3N].
Example 2
Into a dry two-necked flask were charged 53.42g of ethylene glycol, 3.02g of precipitated silica, 9.00g of triethanolamine and 4.59g of 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU), followed by nitrogen substitution, reaction at 200℃for 10 hours and distillation under reduced pressure at 160℃to remove ethylene glycol. Cooling to 50 ℃, adding 21.02g of ethanol into the residue, stirring for 1h, filtering, washing the solid with ethanol for 2 times, and drying at 60 ℃ to obtain 6.8g of solid product. The yield thereof was found to be about 66.25%.
Example 3
To the dried two-necked flask, 55.89g of ethylene glycol, 3.00g of silicic acid, 9.39g of triethanolamine and 2.16g of imidazole were charged, and after the substitution with nitrogen, the mixture was reacted at 200℃for 8 hours, and the ethylene glycol was distilled off under reduced pressure at 160 ℃. Cooling to 50 ℃, adding 20.43g of ethanol into the residue, stirring for 1h, filtering, washing the solid with ethanol for 2 times, and drying at 60 ℃ to obtain 4.0g of solid product, wherein the yield is about 57.3%.
Example 4
To the two-necked flask dried, 69.21g of ethylene glycol, 3.97g of silicic acid, 10.01g of triethanolamine and 1.91g of imidazole were added, and after nitrogen substitution, the mixture was reacted at 200℃for 12 hours, and then distilled off under reduced pressure at 160 ℃. Cooling to 50 ℃, adding 24.23g of ethanol into the residue for dissolution, stirring for 1h, filtering, washing the solid with ethanol for 2 times, and drying to obtain 6.35g of solid product, wherein the yield is about 61.20%.
Example 5
To a dry two-necked flask were added 73.96g of ethylene glycol, 3.96g of precipitated silica, 15.84g of triethanolamine and 7.03g of 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU), and after nitrogen substitution, the mixture was reacted at 200℃for 10 hours and distilled off under reduced pressure at 160℃to remove ethylene glycol. Cooling to 50 ℃, adding 21.25g of ethanol into the residue for dissolution, stirring for 1h, filtering, washing the solid with ethanol for 2 times, and drying to obtain 7.96g of solid product, wherein the yield is about 63.52%.
Example 6
This example provides an application of 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane as a raw material for preparing tetramethyl silicate.
To a dry two-necked flask were added 33.00g of methanol, 2.01g of the nitrogen-containing organosilicon compound obtained in example 1 and 6.50g of anhydrous calcium chloride, and the mixture was stirred uniformly, 5.0g of methanesulfonic acid was added, and the mixture was stirred under nitrogen at 20℃for 8 hours. After the filtrate was dried with a molecular sieve, the filtrate was filtered, and the filtrate was distilled at 65℃to obtain 28.20g of methanol liquid. Distillation of the remaining liquid at 125℃gave 0.95g of tetramethyl silicate in 63.3% yield.
The infrared spectra of the tetramethyl silicate and the analytically pure tetramethyl silicate obtained in example 6 are shown in FIG. 5, and the infrared characteristic peaks of the product and the analytically pure tetramethyl silicate are consistent.
Claims (7)
1. A process for the preparation of 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane characterized by the steps of: sequentially adding glycol, a silicon source, triethanolamine and a catalyst into a reaction bottle, heating for reaction after nitrogen replacement, filtering after the reaction is completed, removing glycol by reduced pressure distillation after the filtrate is replaced by nitrogen, adding an organic solvent into residues, stirring, filtering, washing and drying to obtain a nitrogen-containing organosilicon compound, wherein the molecular formula of the nitrogen-containing organosilicon compound is as follows: c 14H28O8N2Si2.
2. The method for producing 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane according to claim 1, wherein the silicon source is one or more of precipitated silica and silicic acid.
3. The process for the preparation of 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane according to claim 1, wherein the glycol is ethylene glycol.
4. The process for the preparation of 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane according to claim 1, wherein the molar ratio of silicon source to triethanolamine is 1:1.1-2.
5. The process for the preparation of 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane according to claim 1, wherein the catalyst is one or more of imidazole, 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU); the molar ratio of the silicon source to the catalyst is 1:0.5-1.0.
6. The process for the preparation of 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane according to claim 1, wherein the heating reaction temperature is 190-220 ℃.
7. The method for preparing 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undec-1-yl) oxy) ethane according to claim 1, wherein the organic solvent is one or more of methanol, ethanol and tetrahydrofuran.
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| CN202311827614.2A CN118005670A (en) | 2023-12-26 | 2023-12-26 | Preparation method of 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undecan-1-yl) oxy) ethane |
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| CN202311827614.2A CN118005670A (en) | 2023-12-26 | 2023-12-26 | Preparation method of 1, 2-bis ((2, 8, 9-trioxa-5-aza-1-silabicyclo [3.3.3] undecan-1-yl) oxy) ethane |
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