CN115784157A - Preparation method of decahydrodecaboron diammonium salt - Google Patents
Preparation method of decahydrodecaboron diammonium salt Download PDFInfo
- Publication number
- CN115784157A CN115784157A CN202211502926.1A CN202211502926A CN115784157A CN 115784157 A CN115784157 A CN 115784157A CN 202211502926 A CN202211502926 A CN 202211502926A CN 115784157 A CN115784157 A CN 115784157A
- Authority
- CN
- China
- Prior art keywords
- ammonia gas
- diammonium salt
- preparation
- reaction
- double decomposition
- 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.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000007787 solid Substances 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 21
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims abstract description 5
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910010277 boron hydride Inorganic materials 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- 238000001035 drying Methods 0.000 claims description 11
- 238000005406 washing Methods 0.000 claims description 9
- 239000012065 filter cake Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 238000005649 metathesis reaction Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 238000009776 industrial production Methods 0.000 abstract description 8
- 239000002994 raw material Substances 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000003380 propellant Substances 0.000 description 3
- CRUILBNAQILVHZ-UHFFFAOYSA-N 1,2,3-trimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1OC CRUILBNAQILVHZ-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000006104 solid solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- -1 boron hydride anions Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229940030010 trimethoxybenzene Drugs 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Images
Abstract
The invention relates to a preparation method of decahydrodecaborane diammonium salt, belonging to the technical field of compound synthesis. The preparation method of the decahydrodecaborane diammonium salt comprises the following steps: carrying out double decomposition reaction on decaborane dodecahydride bis-diethyl thioether and ammonia gas in an organic solvent to obtain the boron hydride bis-diethyl thioether. The preparation method of the decahydrododecahydrobisammonium salt takes decahydrododecahydrobisdiethyl sulfide and ammonia gas as raw materials, and white solid decahydrododecahydrobisammonium salt can be prepared through one-step double decomposition reaction. According to the method, the ammonia gas is used for carrying out the double decomposition reaction, so that the normal-temperature operation is realized, the low-temperature operation in the prior art that liquid ammonia is used as a raw material is avoided, the safe production index is improved, and the industrial production is favorably realized.
Description
Technical Field
The invention belongs to the technical field of synthesis of decahydrodecaboron diammonium salt, and particularly relates to a preparation method of decahydrodecaboron diammonium salt.
Background
The polyhedral boron hydride has aromaticity, heat resistance and excellent chemical stability due to the delocalization effect of boron cage electrons, and is applied to a plurality of fields of high-energy fuels, functional materials, biological medicines, catalysts and the like. The commonly used polyhedral boron hydrides are mainly classified into boranes, carboranes and ionic compounds thereof.
The ionic borohydride type ultrahigh-burning-rate regulator has the advantages of high burning heat value, low toxicity, good stability and the like. Compared with carborane, the compound has the characteristics of convenient synthesis and lower cost, so that the preparation and application research of the compound is started in the seventies of the twentieth century in countries such as the United states, and the compound can be used for both a composite propellant and a double-base propellant to remarkably improve the burning rate of the propellant.
Preparation of polyhedral boron hydride anions from borohydrides is generally carried out by pyrolysis of tetraalkylammonium borohydrides in high-boiling solvents, such as decahydrodecaboron anions [ B 10 H 10 ] 2- And the like. In the prior art, typically 10g of decaborane (B) is used 10 H 14 ) Dissolving in dimethyl sulfide (DMS), stirring at room temperature for 3 days, removing excessive DMS, cooling to-78 deg.C, introducing liquid ammonia, and reacting to obtain decahydrodecaboron diammonium salt ((NH) 4 ) 2 B 10 H 10 ) (inorg. Chem.,2020,59 (16), 11449) having the formula:
the preparation method is operated at a low temperature of-78 ℃, has high requirements on equipment and is not easy for industrial production. Therefore, it is necessary to provide a preparation method which is simple and easy to operate, has high safety, and can realize industrial production.
Disclosure of Invention
The invention aims to provide a preparation method of decahydrodecaborane diammonium salt, which solves the problems of harsh operating environment and difficult industrial production in the prior art.
In order to realize the purpose, the invention adopts the technical scheme that:
a preparation method of decahydrodecaboron diammonium salt comprises the following steps: carrying out double decomposition reaction on decaborane-dodecahydride-diethyl sulfide and ammonia gas in an organic solvent to obtain the catalyst. The reaction formula is shown as formula 1.
(Et 2 S) 2 B 10 H 12 +2NH 3 →(NH 4 ) 2 B 10 H 10 +2Et 2 S is formula 1.
The method for preparing decahydrododecahydrobisdiethyl ammonium salt comprises the step of preparing decahydrododecahydrobisdiethyl thioether ((Et) 2 S) 2 B 10 H 12 ) And ammonia (NH) 3 ) The white solid decahydrodecaborane diammonium salt can be prepared by one-step double decomposition reaction of the raw materials. The method adopts ammonia gas for double decomposition reaction, realizes normal temperature operation, avoids low temperature (-78 ℃) operation using liquid ammonia as a raw material in the prior art, improves the safe production index, and is beneficial to realizing industrial production.
And further mixing the dodecahydrododecahydrododecadiethyldecaborane with an organic solvent, introducing ammonia gas for double decomposition reaction, and purifying after the reaction is finished.
Further, in order to gradually and sufficiently react the ammonia gas with the decaborane dodecahydride bis-diethyl sulfide, the flow rate of the ammonia gas is introduced at 0.1 to 10mL/min.
Further, in order to fully react the ammonia gas with the decaborane dodecahydro bis-diethyl sulfide, the time for introducing the ammonia gas is 1-8 h.
Further, in order to more sufficiently and efficiently react decaborododecahydrobisdiethylsulfide with ammonia gas. The organic solvent is one or more of toluene, acetonitrile or alcohol.
Further, the temperature of the double decomposition reaction is 0-35 ℃. The raw materials used in the method are decaborane dodecahydride bis-diethyl thioether and ammonia gas, and the double decomposition reaction can be operated at normal temperature without the low-temperature environment of minus 78 ℃ in the prior art. The reaction is simple and easy to operate, has high safety, and is suitable for large-scale production.
Further, in order to disperse the decaborane dodecahydride bis-diethyl sulfide in the organic solvent more sufficiently, the mass ratio of the decaborane dodecahydride bis-diethyl sulfide to the organic solvent is 2 to 10.
Further, the purification method comprises the following steps: and evaporating the reaction solution obtained by the double decomposition reaction to obtain a solid, washing the solid by using toluene, filtering, and drying a filter cake to obtain the catalyst.
Furthermore, in order to efficiently obtain high-purity decahydrododecaboron diammonium salt, the washing solvent is one or more of toluene, acetonitrile or alcohol.
The invention has the beneficial effects that:
compared with the low-temperature (-78 ℃) operation of the prior art (Inorg. Chem.,2020,59 (16), 11449), the preparation method of decahydrodecaborane diammonium salt provided by the invention is operated at normal temperature, has low requirements on equipment, reduces production cost and improves production safety; in addition, the method has high reaction yield, high purity of the obtained product, suitability for large-scale industrial production and good industrial application prospect.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of a bisammonium decahydrodecaboron salt obtained in example 1;
FIG. 2 is a NMR chart of a C.dbarnmonium decahydrodecaborate salt prepared in example 1.
Detailed Description
The invention will be further explained with reference to the following examples and drawings.
Example 1
The preparation method of the decahydrodecaborane diammonium salt comprises the following steps: 100g of dodecahydrododecadiethyldecaborane and 1L of methanol were charged into a 2L four-necked flask and stirred to obtain an insoluble solid white turbid solution. And (3) introducing ammonia gas into the four-mouth bottle at the temperature of 30 ℃ at the flow rate of 0.35mL/min, wherein heat is released in the ammonia gas introduction process, and the solid is gradually dissolved and finally dissolved. After introducing ammonia gas for 2h, determining the reaction end point by TLC, after the reaction is finished, distilling and spin-drying the reaction solution under reduced pressure to obtain a white solid, washing the white solid with 500mL of methanol, filtering, and drying a filter cake to obtain 57.5g of white crystalline powder.
Performing nuclear magnetic characterization on the obtained white crystalline powder, respectively taking deuterated methanol and trimethoxybenzene as internal standards, and measuring nuclear magnetic resonance hydrogen spectrum as shown in figure 1The carbon spectrum is shown in FIG. 2. From the nuclear magnetic hydrogen spectrum, the white crystalline powder contained 1.5 crystal waters due to (NH) 4 ) 2 B 10 H 10 Form crystal with crystal water (NH) when meeting water 4 ) 2 B 10 H 10 ·1.5H 2 And O. The content of decahydrodecaboron diammonium salt is 98.6%, and the yield is 94.1%.
Example 2
The preparation method of the decahydrodecaborane diammonium salt comprises the following steps: to a 500mL four-necked flask were added 10g of dodecaborododecahydrobisdiethylsulfide and 100mL of toluene to obtain an insoluble solid white turbid solution. And (3) introducing ammonia gas into the four-mouth bottle at the temperature of 20 ℃ at the flow rate of 0.5mL/min, wherein heat is released in the ammonia gas introduction process, and the solid is gradually dissolved and finally dissolved. After ammonia gas is introduced for 1h, TLC is adopted to determine the reaction end point, after the reaction is finished, the reaction liquid is subjected to reduced pressure distillation and spin-drying to obtain white solid, the white solid is washed by 50mL of toluene and filtered, and the filter cake is dried to obtain 5.9g of white crystalline powder, the content of decahydrodecaborane diammonium salt is 98.3%, and the yield is 96.3%.
Example 3
The preparation method of the decahydrodecaborane diammonium salt comprises the following steps: to a 100mL four-necked flask were added 10g of decaborododecahydrobis diethyl sulfide and 30mL of acetonitrile to obtain an insoluble white turbid solid solution. And (3) introducing ammonia gas into the four-mouth bottle at the temperature of 10 ℃ at the flow rate of 2mL/min, wherein heat is released in the process of introducing the ammonia gas, and the solid is gradually dissolved and finally dissolved. And (3) introducing ammonia gas for 1h, determining a reaction end point by adopting TLC (thin layer chromatography), after the reaction is finished, distilling and spin-drying the reaction liquid under reduced pressure to obtain a white solid, washing the white solid by using 300mL of acetonitrile, filtering, and drying a filter cake to obtain 5.9g of white crystalline powder, wherein the content of decahydrodecaborane diammonium salt is 99.1%, and the yield is 97.0%.
Example 4
The preparation method of decahydrodecaboronium salt of the embodiment comprises the following steps: 100g of dodecahydrododecadiethyldecaborane sulfide and 1.2L of ethanol were added to a 2L four-necked flask to obtain an insoluble white turbid solid solution. And (3) introducing ammonia gas into the four-mouth bottle at the flow rate of 0.1mL/min at the temperature of 0 ℃, wherein the ammonia gas is released in the process, and the solid is gradually dissolved and finally dissolved clearly. And (3) introducing ammonia gas for 5h, determining a reaction end point by adopting TLC (thin layer chromatography), after the reaction is finished, distilling and spin-drying the reaction solution under reduced pressure to obtain a white solid, washing the white solid by using 500mL of toluene, filtering, and drying a filter cake to obtain 57.0g of white crystalline powder, wherein the content of decahydrodecaborane diammonium salt is 97.6%, and the yield is 92.4%.
Example 5
The preparation method of the decahydrodecaborane diammonium salt comprises the following steps: 5kg of dodecahydrododecahydrododecadiethylsulfide decaborane and 25L of toluene are added into a 50L reaction kettle to obtain solid insoluble white turbid solution, ammonia gas is introduced into a four-mouth bottle at the temperature of 20 ℃ at the flow rate of 10mL/min, heat release occurs in the process of introducing the ammonia gas, the solid is gradually dissolved, and the solid is finally dissolved to be clear. And (3) introducing ammonia gas for 8 hours, determining a reaction end point by adopting TLC, after the reaction is finished, carrying out reduced pressure distillation and spin-drying on the reaction liquid to obtain a white solid, washing the white solid by using 500mL of toluene, filtering, and drying a filter cake to obtain 2.8kg of white crystalline powder, wherein the content of decahydrodecaborane diammonium salt is 96.5%, and the yield is 89.7%.
The method takes decahydrododecahydrobisdiethylsulfide and ammonia gas as raw materials to prepare white solid decahydrododecahydrobisammonium salt through one-step reaction. According to the method, the ammonia gas is used for carrying out the double decomposition reaction, so that the normal-temperature operation is realized, the low-temperature operation in the prior art that liquid ammonia is used as a raw material is avoided, the safe production index is improved, and the industrial production is favorably realized. The preparation method of decahydrodecaborane diammonium salt is operated at normal temperature, and has low requirements on equipment compared with low-temperature operation; the obtained product has high purity and high yield, is suitable for large-scale industrial production, and has good industrial application prospect.
Claims (9)
1. A preparation method of decahydrodecaboron diammonium salt is characterized by comprising the following steps: carrying out double decomposition reaction on decaborane dodecahydride bis-diethyl thioether and ammonia gas in an organic solvent to obtain the boron hydride bis-diethyl thioether.
2. The method for preparing decahydrododecahydrobisammonium salt according to claim 1, wherein the decahydrododecahydrobisdiethyl sulfide is mixed with an organic solvent, ammonia gas is introduced for a double decomposition reaction, and the mixture is purified after the reaction is finished.
3. The method for preparing decahydrodecaborane diammonium salt according to claim 1, characterized in that the flow rate of the introduced ammonia gas is 0.1-10 mL/min.
4. The method according to claim 1 or 3, wherein the time for introducing the ammonia gas is 1 to 8 hours.
5. The method for preparing decahydrodecaboron diammonium salt according to claim 1, wherein the organic solvent is one or more of toluene, acetonitrile or alcohol.
6. The method of claim 1, wherein the metathesis reaction is carried out at a temperature of 0 to 35 ℃.
7. The method for producing a decahydrododecahydrobisammonium salt according to claim 1, wherein the mass ratio of the decahydrododecahydrobisdiethyl sulfide to the organic solvent is 2 to 10.
8. The method for preparing decahydrodecaborane diammonium salt according to claim 1, characterized in that the purification method is: and evaporating the reaction solution obtained by the double decomposition reaction to dryness to obtain a solid, washing and filtering the solid by using a washing solvent, and drying a filter cake to obtain the catalyst.
9. The method for preparing decahydrodecaboron diammonium salt according to claim 8, wherein the washing solvent is one or more of toluene, acetonitrile or alcohol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211502926.1A CN115784157A (en) | 2022-11-28 | 2022-11-28 | Preparation method of decahydrodecaboron diammonium salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211502926.1A CN115784157A (en) | 2022-11-28 | 2022-11-28 | Preparation method of decahydrodecaboron diammonium salt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115784157A true CN115784157A (en) | 2023-03-14 |
Family
ID=85442267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211502926.1A Pending CN115784157A (en) | 2022-11-28 | 2022-11-28 | Preparation method of decahydrodecaboron diammonium salt |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115784157A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104017010A (en) * | 2014-06-24 | 2014-09-03 | 西安近代化学研究所 | Preparation method of n-hexyl carborane |
| CN104497031A (en) * | 2014-12-13 | 2015-04-08 | 西安近代化学研究所 | Preparation method of alkyl carborane derivatives |
| WO2015117123A1 (en) * | 2014-02-03 | 2015-08-06 | The Curators Of The University Of Missouri | Synthesis of amine boranes and polyhedral boranes |
| CN108912158A (en) * | 2018-08-27 | 2018-11-30 | 河南师范大学 | A kind of Novel boron cluster caged Mn [B10H9- 1-X] compound and preparation method thereof |
| CN114015059A (en) * | 2021-11-10 | 2022-02-08 | 中国科学院宁波材料技术与工程研究所 | High boron content carborane polymer and synthetic method thereof |
-
2022
- 2022-11-28 CN CN202211502926.1A patent/CN115784157A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015117123A1 (en) * | 2014-02-03 | 2015-08-06 | The Curators Of The University Of Missouri | Synthesis of amine boranes and polyhedral boranes |
| CN104017010A (en) * | 2014-06-24 | 2014-09-03 | 西安近代化学研究所 | Preparation method of n-hexyl carborane |
| CN104497031A (en) * | 2014-12-13 | 2015-04-08 | 西安近代化学研究所 | Preparation method of alkyl carborane derivatives |
| CN108912158A (en) * | 2018-08-27 | 2018-11-30 | 河南师范大学 | A kind of Novel boron cluster caged Mn [B10H9- 1-X] compound and preparation method thereof |
| CN114015059A (en) * | 2021-11-10 | 2022-02-08 | 中国科学院宁波材料技术与工程研究所 | High boron content carborane polymer and synthetic method thereof |
Non-Patent Citations (1)
| Title |
|---|
| E. L. MUETTERTIES ET AL.: "Chemistry of Boranes. VIII. Salts and Acids of B10H10-2 and B12H12-2", 《INORGANIC CHEMISTRY》, vol. 3, no. 3, pages 444 - 451 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110878104B (en) | Preparation method of chiral 1, 2-bis (2, 5-diphenylphosphino) ethane | |
| CN115784157A (en) | Preparation method of decahydrodecaboron diammonium salt | |
| CN111087274B (en) | Method for preparing bis (norbornadiene) rhodium tetrafluoroborate | |
| CN101973537A (en) | Method for preparing transition metal phosphide | |
| Adams et al. | Cluster synthesis. 35. On the way to high-nuclearity platinum-osmium cluster complexes. Synthesis and structural characterizations of Pt2Os3 (CO) 9 (COD) 2 (. mu.-H) 2 and Pt4Os6 (CO) 21 (COD)(. mu.-H) 2 (COD= cycloocta-1, 5-diene) | |
| CN110105160B (en) | Preparation method based on triphenylene alkyne type precursor and polycyclic aromatic hydrocarbon derivative thereof | |
| Kriz et al. | Clusters as Substituents. Synthesis and Thermal Decomposition of Metal Carboranecarboxylates | |
| CN108329360B (en) | Ferrocene picrate ionic compound and preparation method thereof | |
| CN113666928A (en) | Preparation method of novel lovaene-2N with nitrogen atoms doped on serrated edge | |
| CN115676800B (en) | Preparation method of lithium difluorophosphate | |
| CN116655674B (en) | Method for synthesizing high-abundance boron 10 isotope biboronate | |
| CN105949229A (en) | Synthetic method of B-substituted aminoborane | |
| CN111689998B (en) | Synthesis method of bis (ethylamino) dicyclopentyl silane | |
| CN107098357B (en) | Preparation method of octahydro-triboric acid compound | |
| CN114632552B (en) | Buchwald pre-catalyst, preparation method and application thereof | |
| CN117735567A (en) | Borane compound NH 3 B 3 H 7 Is synthesized by the method of (2) | |
| CN112010320B (en) | Preparation method of B-substituted cyano sodium borohydride | |
| CN117263197A (en) | Boron hydrogen compound ammonium salt NH 4 B 9 H 14 Is synthesized by the method of (2) | |
| CN115417777A (en) | Preparation method of (S) -2-ethyl-N- (1-methoxy-2-propyl) -6-methylaniline | |
| CN117924328A (en) | Metal oxygen cluster compound of boropyrazole ligand, and preparation method and application thereof | |
| CN113666383A (en) | Boron-nitrogen-hydrogen compound K [ B ]3H7NH2BH2NH2B3H7]Method of synthesis of | |
| CN114605476A (en) | Preparation method of allyl palladium chloride dimer | |
| CN115340563A (en) | Preparation method of allyl boron compound and zinc-catalyzed cyclopropene | |
| CN115181119A (en) | Synthesis method of borane compound BN hexa-heterocyclic compound | |
| CN117263198A (en) | Borane compound NH 3 B 9 H 13 Synthetic method and application of (2) |
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 |