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Lithium aluminum hydride powder is an inorganic compound with the chemical formula of LiAlH4, CAS 16853-85-3. It is a white crystalline powder, insoluble in hydrocarbons, soluble in ether, tetrahydrofuran, soluble in tetrahydrofuran, ether and dimethyl solvent, slightly soluble in dibutyl ether, and almost insoluble in dioxane and hydrocarbon compounds. Lithum aluminm hydride is stable in dry air, and violently hydrolyzes in humid air, releasing a large amount of H2 and burning. It can reduce ketones, aldehydes, acids, esters, anhydrides, quinones, etc. to alcohols, halogenated hydrocarbons to hydrocarbons, and nitriles to primary amines. Lithum aluminm hydride is widely used in medicine, pesticides, spices, dyes and other industries due to its excellent reducibility, and is used as a reducing agent in other organic synthesis. At the same time, lithum aluminm hydride will release a lot of heat energy when burning, and it is also used as an additive for missiles and launch vehicles.
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We can ship under the real name! Lithium Aluminum Hydride, CAS 16853-85-3 HS code: 2850009090
Explanation for the real name shipping: |
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Chemical Formula |
AlH4Li |
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Exact Mass |
38 |
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Molecular Weight |
38 |
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m/z |
38 (100.0%), 37 (8.2%) |
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Elemental Analysis |
Al, 71.09; H, 10.62; Li, 18.29 |
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Analysis of the multiple uses of lithium aluminum hydride powder: from organic synthesis to cutting-edge technology
Lithum aluminum hydride (LiAlH ₄), as a white to pale yellow crystalline powder, exhibits irreplaceable value in organic synthesis, new energy materials, pharmaceuticals, aerospace, nuclear industry and other fields due to its strong reducibility and unique chemical properties. This article will start from its core applications, combine industry practice and cutting-edge exploration, and systematically sort out the diverse application scenarios of lithum aluminum hydride.
Lithum aluminum hydride is one of the most important reducing agents in organic chemistry, with a reducing ability far exceeding that of similar reagents such as sodium borohydride. It can efficiently reduce various oxygen-containing and nitrogen-containing functional groups
Reduction of carbonyl compounds
Lithum aluminum hydride can reduce aldehydes and ketones to primary and secondary alcohols under mild reaction conditions (can be carried out at room temperature), with a yield of over 90%. For example, in the process of synthesizing the antidepressant drug fluoxetine, lithum aluminum hydride can reduce key intermediate ketones to alcohols, providing active groups for subsequent steps.
Deep reduction of esters and amides
Traditional reducing agents are difficult to reduce esters to alcohols, while lithum aluminum hydride can overcome this limitation by directly converting ester groups to primary alcohols.
When synthesizing the analgesic ibuprofen, lithum aluminum hydride is used to reduce ester groups, simplify the synthesis route, and improve yield. In addition, it can also reduce amides to amines, providing a key tool for the preparation of amino acids and peptide compounds.
Special functional group conversion
Nitrile reduction: converting nitrile groups into primary amines for the synthesis of antiepileptic drug carbamazepine.
Halogenated hydrocarbon dehalogenation: In inert solvents, lithum aluminum hydride can remove halogens from halogenated hydrocarbons and generate hydrocarbon compounds.
Reduction of nitro compounds: Reduce aromatic nitro compounds to azo compounds for further use in dye synthesis.
Case: When synthesizing the anti AIDS drug itravirin, lithum aluminum hydride reduced the ester group of the key intermediate, shortening the reaction steps from 5 to 3, and increasing the total yield by 25%.
Lithium aluminum hydride is not only used as a synthetic raw material in the pharmaceutical field, but also directly participates in drug research and development, but its toxicity needs to be strictly controlled:
Synthesis of drug intermediates
Antibiotics: In the synthesis of cephalosporin antibiotics, lithum aluminum hydride is used to reduce side chain ester groups and generate active alcohol groups.
Antitumor drugs: The synthesis of paclitaxel side chains relies on the reduction of ketone groups by lithum aluminum hydride, ensuring the binding activity between the drug and microtubule proteins.
Exploration of direct medicinal use
Acid fast treatment: Lithum aluminum hydride can neutralize gastric acid (pH=1.5-3.5) and alleviate symptoms of gastric ulcers. But its strong alkalinity (pKa ≈ 36) can easily cause diarrhea, and it has gradually been replaced by aluminum magnesium carbonate isothermal and formulation in clinical practice.
Anti inflammatory and analgesic: Laboratory studies have shown that lithum aluminum hydride can inhibit COX-2 enzyme activity and reduce the levels of inflammatory factors (IL-6, TNF - α) in rheumatoid arthritis model mice by 30% -50%, but it has not yet entered clinical practice due to toxicity issues.
Risk warning: The LD ₅₀ (oral administration to rats) of lithum aluminum hydride is 100 mg/kg, which is a highly toxic substance. The hydrolysis product aluminum hydroxide may deposit in brain tissue, causing neurotoxicity, so pharmaceutical applications must strictly follow GMP standards.
The lightweight and high-energy properties of lithum aluminum hydride make it a key raw material for high-end manufacturing:
Rocket propellant
Burning 1 kg of lithum can release 42998 kJ of heat, which is 20000 times that of coal. Lithum aluminum hydride, as a solid propellant additive, can increase the specific impulse (from 250 s to 280 s) and reduce rocket launch costs. Some models of China's Long March series rockets have adopted composite propellants containing lithum aluminum hydride.
Nuclear reactor control rod
The neutron absorption cross section of lithum aluminum hydride (σ=0.3 bar) is moderate and can be used to regulate the power of nuclear reactors. The control rods of the EPR nuclear power plant in France are made of lithum aluminum hydride boron carbon composite material to achieve precise temperature control.
Satellite hydrogen storage for energy supply
In low orbit satellites, the lithum aluminum hydride hydrogen storage system can provide a hydrogen source for fuel cells, with a battery life three times longer than traditional lithum batteries. The European Copernicus environmental monitoring satellite has applied this technology.
The 'secret weapon' of industrial catalysis and material modification
The strong reducibility and alkalinity of lithum aluminum hydride make it a catalyst or additive for various industrial processes
Catalyst for polymerization reaction
In butadiene polymerization, lithum aluminum hydride can regulate the molecular weight distribution of the polymer (Mw/Mn reduced from 3.0 to 1.5), enhancing the tear strength of the rubber. China Zhongce Rubber Group has applied it to the production of high-performance tires, increasing wear resistance by 20%.
Metal refining deoxidizer
In copper smelting, adding 0.001% lithum aluminum hydride can remove oxygen impurities (from 50 ppm to 5 ppm) and increase conductivity to 101% IACS (International Annealed Copper Standard). After Jiangxi Copper Group adopted this technology, the export qualification rate of copper materials increased from 92% to 98%.
Ceramic material sintering additive
Lithum aluminum hydride can lower the sintering temperature of silicon nitride ceramics (from 1800 ℃ to 1600 ℃), while suppressing abnormal grain growth, increasing the bending strength of ceramics from 800 MPa to 1200 MPa. Kyocera Corporation of Japan uses it for high-end tool production, extending its service life by 50%.
With technological breakthroughs, the application of lithum aluminum hydride in emerging fields is expanding:
Quantum computing materials
Lithum aluminum hydride thin film can be used as a substrate material for superconducting quantum bits, and its low dielectric constant (ε ≈ 3) can reduce signal loss. The IBM quantum computing team's experiment shows that this material extends the coherence time of quantum bits to 100 μ s.
3D printing of metal powder
Aluminum alloy powder coated with lithum aluminum hydride (such as AlSi10Mg) can suppress thermal cracks during selective laser melting (SLM) process, and the density of printed parts can reach 99.9%. EOS, a German company, has commercialized it for the manufacturing of aircraft engine blades.
Flexible electronic devices
Lithium aluminum hydride and polydimethylsiloxane (PDMS) composite can be used to prepare conductive elastomers (with a conductivity of 10 S/m) for wearable device electrodes. The flexible sensor developed by the Samsung team in South Korea is based on this material, with a resistance change of only 5% when the tensile rate reaches 300%.
From the "universal reducing agent" of organic synthesis to the "potential material" of quantum computing, lithum aluminum hydride continues to drive technological progress with its unique chemical properties. In the future, with the improvement of green synthesis technology and safety protection system, its application boundaries will be further expanded, providing key support for human exploration of new energy, new materials, and high-end manufacturing fields. However, finding a balance between efficiency and safety remains the core proposition in the industrialization process of lithum aluminum hydride.
The chemical properties of lithium aluminum hydride powder are shown in the following aspects:
Lithium aluminum hydride is metastable at room temperature. During long-term storage, lithum aluminm hydride will be decomposed into Li3AlH6 and LiH. This process can be accelerated by such cocatalytic elements as titanium, iron and vanadium. When heating lithum aluminm hydride, the reaction mechanism is divided into three steps:
3LiAlH4 → Li3AlH6 + 2Al + 3H2↑(R1)
2Li3AlH6 → 6LiH + 2Al + 3H2↑(R2)
2LiH + 2Al → 2LiAl +H2↑(R3)
R1 usually starts with the melting of lithium aluminm hydride, with a temperature range of 150~170 ℃, and then decomposes into Li3AlH6 immediately, but R1 is carried out below the melting point of LiAlH4. At about 200 ℃, Li3AlH6 decomposes into LiH and Al (R2), and then decomposes into LiAl (R3) above 400 ℃. In practice, reaction R1 is irreversible, while R3 is reversible, and the equilibrium pressure at 500 ℃ is 25 kPa. The reaction of R1 and R2 can occur at room temperature with appropriate catalyst.
LiAlH4 reacts violently and explosively with water and releases hydrogen:
LiAlH4 + 2H2O → LiAlO2 + 4H2↑
LiAlH4 + 4H2O → LiOH +Al(OH)3+ 4H2↑
Since the hydrogen released is quantitative, this reaction can be used to determine the content of lithum aluminum hydride in the sample. In order to prevent the reaction from being too violent, some dioxane, ethylene glycol dimethyl ether or tetrahydrofuran are often added as the diluent. This reaction provides a useful laboratory method for hydrogen production. The samples exposed to air for a long time will usually turn white because the samples have absorbed enough water to form a white mixture consisting of lithum hydroxide and aluminum hydroxide.
The ether or tetrahydrofuran solution of LiAlH4 can react violently with ammonia to release hydrogen:
LiAlH4+4NH3 → LiAl (NH2) 4+2H2 ↑
When the amount of ammonia is insufficient, the following reaction occurs:
2LiAlH4+5NH3 → [LiAlH (NH2) 2] 2NH+6H2 ↑
When the NH3/LiAlH4 ratio is smaller, all three hydrogen in ammonia can be replaced:
3LiAlH4+NH3 → (LiAlH3) 3N+3H2 ↑
Lithium aluminm hydride can react with almost all halides to generate corresponding coordination aluminum hydride. When the coordination aluminum hydride is unstable, it will be decomposed into corresponding hydride. The general formula is:
nLiAlH4+MXn → M (AlH4) n+nLiX, M (AlH4) n → MHn+nAlH3
Therefore, many metal or non-metallic hydrides can be prepared by this method, such as
LiAlH4+4NaCl → 4NaH+LiCl+AlCl3
Lithum aluminm hydride can conduct double decomposition reaction with NaH in tetrahydrofuran to efficiently produce sodium aluminum hydride (NaAlH4):
LiAlH4+NaH → NaAlH4+LiH
Potassium aluminum hydride (KAlH4) can be prepared in a similar way with diethylene glycol dimethyl ether as solvent:
LiAlH4+KH → KAlH4+LiH
Lithium aluminum hydride can reduce many organic compounds, and its ether or tetrahydrofuran solution is commonly used in practice. The reduction ability of lithium aluminm hydride is stronger than that of the related sodium borohydride, because the Al-H bond is weaker than the B-H bond. Due to inconvenient storage and use, bis (2-methoxyethoxy) sodium aluminum hydride (red aluminum), a derivative of lithum aluminm hydride, is commonly used as a reducing agent in industry, but lithum aluminm hydride is still used in small-scale industrial production.
The functional groups that can be reduced by lithium aluminum hydride powder mainly include:
Haloalkanes are reduced to alkanes. The reaction of iodoalkanes is the fastest, followed by bromoalkanes and chloroalkanes. In this reaction, the primary haloalkanes (primary haloalkanes) have good performance, and the obtained products undergo configuration transformation, so this reaction is considered to be SN2 mechanism. The secondary halogenated alkanes (secondary halogenated alkanes) can also be reduced by this method. The tertiary halogenated hydrocarbons (tertiary halogenated alkanes) are prone to elimination reaction, so this method is not applicable. Lithum aluminm hydride can only be used to reduce alkynes with alcohol groups nearby, and cannot be used to reduce simple olefins and aromatic hydrocarbons.
Silicon halides are reduced to silane, such as
LiAlH4+SiCl4 → SiH4+LiCl+AlCl3
Carbonyl compounds (except amides) are reduced to alcohols, such as esters and carboxylic acids can be reduced to primary alcohols by lithum aluminm hydride. Before the discovery of the method of reducing esters by lithum aluminm hydride, the ester was generally reduced by the Bouver Brown reduction reaction, that is, boiling metal sodium anhydrous alcohol as the reducing agent, but this reaction is difficult to carry out. Aldehydes and ketones can also be reduced to alcohols by lithium aluminm hydride, but more mild reagents such as NaBH4 are generally used for reduction. α,β- Unsaturated ketones will be reduced to allyl alcohol.
Epoxy compound. When the epoxy compound is reduced, lithum aluminm hydride reagent will attack the low steric hindrance end of the epoxy compound, usually generating secondary or tertiary alcohols. Cyclohexane oxide will be preferentially reduced to α Alcohols of bonds (upright bonds).
Amides and imides are reduced to amines. The yield of such reactions is generally high, and the reaction of N, N-substituted raw materials is much faster than others.
Nitrile is reduced to primary amine. In addition, oximes, nitro compounds and alkyl azides can be reduced to amines. Quaternary ammonium cations can be reduced to corresponding tertiary amines.
Reaction with alcohol to produce alkoxy lithium aluminm hydride:
LiAlH4 + ROH → LiAl(OR)H3 + H2↑
LiAlH4 + 2ROH → LiAl(OR)2H2 + 2H2↑
LiAlH4 + 3ROH → LiAl(OR)3H + 3H2↑
LiAl (OR)2H2 is a suitable reagent for reducing amides to aldehydes, LiAl(OC(CH3)3)3H is a suitable reagent for reducing acyl chlorides to aldehydes, and lithium aluminm hydride cannot partially reduce acyl chlorides to corresponding aldehydes, because lithum aluminm hydride can completely reduce the latter to primary alcohol, so it is necessary to use a milder tri tert butyloxy lithum aluminm hydride (LiAl(OC(CH3)3)3H) to reduce acyl chlorides. The reaction of lithum tri tert butoxy aluminum hydride with acyl chloride is much faster than that with aldehyde. For example, the addition of sulfoxide chloride in isovaleric acid will generate isovaleryl chloride. At this time, lithium aluminum hydride powder can be used to reduce isovaleryl chloride to isovaleraldehyde, and the yield can reach 65%.
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