Aluminium hydride

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Aluminium hydride
Aluminium-hydride-unit-cell-3D-vdW.png
Names
Preferred IUPAC name
Aluminium hydride
Systematic IUPAC name
Alumane
Other names
  • Alane
  • Aluminic hydride
  • Aluminium(III) hydride
  • Aluminium trihydride
  • Trihydridoaluminium
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.029.139 OOjs UI icon edit-ltr-progressive.svg
245
PubChem CID
UNII
  • InChI=1S/Al.3H Yes check.svgY
    Key: AZDRQVAHHNSJOQ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1S/Al.3H
    Key: AZDRQVAHHNSJOQ-UHFFFAOYSA-N
  • InChI=1/Al.3H/rAlH3/h1H3
    Key: AZDRQVAHHNSJOQ-FSBNLZEDAV
  • [AlH3]
Properties
AlH3
Molar mass 30.006 g·mol−1
Appearancewhite crystalline solid, non-volatile, highly polymerized, needle-like crystals
Density 1.477 g/cm3, solid
Melting point 150 °C (302 °F; 423 K) starts decomposing at 105 °C (221 °F)
reacts
Solubility soluble in ether
reacts in ethanol
Thermochemistry
40.2 J/(mol·K)
Std molar
entropy (S⦵298)
30 J/(mol·K)
−11.4 kJ/mol
46.4 kJ/mol
Related compounds
Related compounds
 Lithium aluminium hydride, diborane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Aluminium hydride (also known as alane and alumane) refers to a collection of inorganic compounds with the formula Al H 3. As a gas, alane is a planar molecule. When generated in ether solutions, it exists as an ether adduct. Solutions of alane polymerizes to a solid, which exists in several crystallograhically distinguishable forms. [1]

Structure

Alane can adopt 3-, 4-, or 6-coordination, depending on conditions.

Gaseous alane

Monomeric AlH3 has been isolated at low temperature in a solid noble gas matrix. It was shown to be planar. [2] The dimeric form, Al2H6, has been isolated in solid hydrogen. It is isostructural with diborane (B2H6) and digallane (Ga2H6). [3] [4] [5]

Solid alane

Solid alane, which is colorless and nonvolatile, precipitates from etherial solutions over the course of hours at room temperature. Numerous polymorphs can be obtained, which have been labeled α-, α’-, β-, γ-, ε-, and ζ-alanes. [6] The best characterized solid alane is α-alane. According to X-ray crystallography, adopts a cubic or rhombohedral morphology. It features octahedral AlH6 centers interconnected by Al-H-Al bridges. The Al-H distances are all equivalent (172 pm) and the Al-H-Al angles are 141°. [7] α’-Alane forms needle-like crystals, and γ-alane forms bundles of fused needles.[ citation needed ]

Crystallographic Structure of α-AlH3 [8]
The α-AlH3 unit cell Aluminium coordinationHydrogen coordination
Aluminium-hydride-unit-cell-3D-balls.png Aluminium-hydride-Al-coordination-3D-balls.png Aluminium-hydride-H-coordination-3D-balls.png

Handling

Alane is not spontaneously flammable. [9] Even so, "similar handling and precautions as... exercised for Li[AlH4]" (the chemical reagent, lithium aluminium hydride) are recommended, as its "reactivity [is] comparable" to this related reducing reagent. [1] For these reagents, both preparations in solutions and isolated solids are "highly flammable and must be stored in the absence of moisture". [10] Laboratory guides recommend alane use inside a fume hood. [1] [ why? ] Solids of this reagent type carry recommendations of handling "in a glove bag or dry box". [10] After use, solution containers are typically sealed tightly with concomitant flushing with inert gas to exclude the oxygen and moisture of ambient air. [10]

Passivation [ clarification needed ] greatly diminishes the decomposition rate associated with alane preparations.[ citation needed ] Passivated alane nevertheless retains a hazard classification of 4.3 (chemicals which in contact with water, emit flammable gases). [11]

Reported accidents

Alane reductions are believed to proceed via an intermediate coordination complex, with aluminum attached to the partially reduced functional group, and liberated when the reaction undergoes protic quenching. If the substrate is also fluorinated, the intermediate may instead explode if exposed to a hot spot above 60°C. [12]

Preparation

Aluminium hydrides and various complexes thereof have long been known. [13] Its first synthesis was published in 1947, and a patent for the synthesis was assigned in 1999. [14] [15] Aluminium hydride is prepared by treating lithium aluminium hydride with aluminium trichloride. [16] The procedure is intricate: attention must be given to the removal of lithium chloride.

3 Li[AlH4] + AlCl3 → 4 AlH3 + 3 LiCl

The ether solution of alane requires immediate use, because polymeric material rapidly precipitates as a solid. Aluminium hydride solutions are known to degrade after 3 days. Aluminium hydride is more reactive than Li[AlH4]. [17]

Several other methods exist for the preparation of aluminium hydride:

2 Li[AlH4] + BeCl2 → 2 AlH3 + Li2[BeH2Cl2]
2 Li[AlH4] + H2SO4 → 2 AlH3 + Li2SO4 + 2 H2
2 Li[AlH4] + ZnCl2 → 2 AlH3 + 2 LiCl + ZnH2
2 Li[AlH4] + I2 → 2 AlH3 + 2 LiI + H2

Electrochemical synthesis

Several groups have shown that alane can be produced electrochemically. [18] [19] [20] [21] [22] Different electrochemical alane production methods have been patented. [23] [24] Electrochemically generating alane avoids chloride impurities. Two possible mechanisms are discussed for the formation of alane in Clasen's electrochemical cell containing THF as the solvent, sodium aluminium hydride as the electrolyte, an aluminium anode, and an iron (Fe) wire submerged in mercury (Hg) as the cathode. The sodium forms an amalgam with the Hg cathode preventing side reactions and the hydrogen produced in the first reaction could be captured and reacted back with the sodium mercury amalgam to produce sodium hydride. Clasen's system results in no loss of starting material. For insoluble anodes, reaction 1 occurs, while for soluble anodes, anodic dissolution is expected according to reaction 2:

  1. [AlH4]− − e− + n THF → AlH3·nTHF + 1/2 H2
  2. 3 [AlH4]− + Al − 3 e− + 4n THF → 4 AlH3·nTHF

In reaction 2, the aluminium anode is consumed, limiting the production of aluminium hydride for a given electrochemical cell.

The crystallization and recovery of aluminium hydride from electrochemically generated alane has been demonstrated. [21] [22]

High pressure hydrogenation of aluminium

α-AlH3 can be produced by hydrogenation of aluminium at 10 GPa and 600 °C (1,112 °F). The reaction between the liquified hydrogen produces α-AlH3 which could be recovered under ambient conditions. [25]

Reactions

Formation of adducts with Lewis bases

AlH3 readily forms adducts with strong Lewis bases. For example, both 1:1 and 1:2 complexes form with trimethylamine. The 1:1 complex is tetrahedral in the gas phase, [26] but in the solid phase it is dimeric with bridging hydrogen centres, [(CH3)3NAlH2(μ-H)]2. [27] The 1:2 complex adopts a trigonal bipyramidal structure. [26] Some adducts (e.g. dimethylethylamine alane, (CH3CH2)(CH3)2N·AlH3) thermally decompose to give aluminium and may have use in MOCVD applications. [28]

Its complex with diethyl ether forms according to the following stoichiometry:

AlH3 + (CH3CH2)2O → (CH3CH2)2O·AlH3

Similar adducts are assumed to form when alane is generated in THF from lithium aluminium hydride.

The reaction with lithium hydride in ether produces lithium aluminium hydride:

AlH3 + LiH → Li[AlH4]

Various alanates have been characterized beyond lithium aluminium hydride. They tend to feature five- and six-coordinate Al centers: Na
3AlH
6, Ca(AlH
4))
2, SrAlH
5). [29]

Reduction of functional groups

Alane and its derivatives are reducing reagents in organic synthesis based around group 13 hydrides. [30] In solution—typically in ethereal solvents such tetrahydrofuran or diethyl ether—aluminium hydride forms complexes with Lewis bases, and reacts selectively with particular organic functional groups (e.g., with carboxylic acids and esters over organic halides and nitro groups), and although it is not a reagent of choice, it can react with carbon-carbon multiple bonds (i.e., through hydroalumination). Given its density, and with hydrogen content on the order of 10% by weight, [6] some forms of alane are, as of 2016, [31] active candidates for storing hydrogen and so for power generation in fuel cell applications, including electric vehicles.[ not verified in body ] As of 2006 it was noted that further research was required to identify an efficient, economical way to reverse the process, regenerating alane from spent aluminium product.

In organic chemistry, aluminium hydride is mainly used for the reduction of functional groups. [32] In many ways, the reactivity of aluminium hydride is similar to that of lithium aluminium hydride. Aluminium hydride will reduce aldehydes, ketones, carboxylic acids, anhydrides, acid chlorides, esters, and lactones to their corresponding alcohols. Amides, nitriles, and oximes are reduced to their corresponding amines.

In terms of functional group selectivity, alane differs from other hydride reagents. For example, in the following cyclohexanone reduction, lithium aluminium hydride gives a trans:cis ratio of 1.9 : 1, whereas aluminium hydride gives a trans:cis ratio of 7.3 : 1. [33]

Stereoselective reduction of a substituted cyclohexanone using aluminium hydride Functional Group Reduction 1.svg
Stereoselective reduction of a substituted cyclohexanone using aluminium hydride

Alane enables the hydroxymethylation of certain ketones (that is the replacement of C−H by C−CH2OH at the alpha position). [34] The ketone itself is not reduced as it is "protected" as its enolate.

Functional Group Reduction using aluminium hydride Functional Group Reduction 2.svg
Functional Group Reduction using aluminium hydride

Organohalides are reduced slowly or not at all by aluminium hydride. Therefore, reactive functional groups such as carboxylic acids can be reduced in the presence of halides. [1]

Functional Group Reduction using aluminium hydride Functional Group Reduction 3.svg
Functional Group Reduction using aluminium hydride

Aluminium hydride reduces ester in the presence of nitro groups. [1]

Ester reduction using aluminium hydride Functional Group Reduction 4.svg
Ester reduction using aluminium hydride

Aluminium hydride reduces acetals to half protected diols. [1]

Acetal reduction using aluminium hydride Functional Group Reduction 5.svg
Acetal reduction using aluminium hydride

Aluminium hydride reduces epoxide to the corresponding alcohol: [1]

Epoxide reduction using aluminium hydride Epoxide Ring Opening.jpg
Epoxide reduction using aluminium hydride

The allylic rearrangement reaction carried out using aluminium hydride is a SN2 reaction, and it is not sterically demanding: [1]

Phosphine reduction using aluminium hydride Allylic rearrangement reaction.svg
Phosphine reduction using aluminium hydride

Aluminium hydride will reduce carbon dioxide to methane with heating:[ citation needed ]

4 AlH3 + 3 CO2 → 3 CH4 + 2 Al2O3

Hydroalumination

Akin to hydroboration, aluminium hydride can, in the presence of titanium tetrachloride, add across multiple bonds. [35] [36] When the multiple bond in question is a propargylic alcohols, the results are Alkenylaluminium compounds. [37]

Hydroalumination of 1-hexene Hydroalumination.svg
Hydroalumination of 1-hexene

Fuel

In its passivated form, alane is an active candidate for storing hydrogen, and can be used for efficient power generation via fuel cell applications, including fuel cell and electric vehicles and other lightweight power applications. [38] AlH3 contains up 10.1% hydrogen by weight (at a density of 1.48 grams per milliliter), [6] or twice the hydrogen density of liquid H2.[ citation needed ] As of 2006, AlH3 was described as a candidate for which "further research w[ould] be required to develop an efficient and economical process to regenerate [it] from the spent Al powder". [6] [ needs update ]

Alane is also a potential additive to solid rocket fuel and to explosive and pyrotechnic compositions [ citation needed ] due to its high hydrogen content and low dehydrogenation temperature. [38] In its unpassivated form, alane is also a promising rocket fuel additive, capable of delivering impulse efficiency gains of up to 10%. [39] However, AlH3 can degrade when stored at room temperature, and some of its crystal forms have "poor compatibility" with some fuel components. [38]

Deposition

Heated alane releases hydrogen gas and produces a very fine thin film of aluminum metal. [40]

Related Research Articles

<span class="mw-page-title-main">Hydride</span> Molecule with a hydrogen bound to a more electropositive element or group

In chemistry, a hydride is formally the anion of hydrogen (H−), a hydrogen ion with two electrons. In modern usage, this is typically only used for ionic bonds, but it is sometimes (and more frequently in the past) been applied to all compounds containing covalently bound H atoms. In this broad and potentially archaic sense, water (H2O) is a hydride of oxygen, ammonia is a hydride of nitrogen, etc. In covalent compounds, it implies hydrogen is attached to a less electronegative element. In such cases, the H centre has nucleophilic character, which contrasts with the protic character of acids. The hydride anion is very rarely observed.

<span class="mw-page-title-main">Diborane</span> Chemical compound

Diborane(6), commonly known as diborane, is the chemical compound with the formula B2H6. It is a highly toxic, colorless, and pyrophoric gas with a repulsively sweet odor. Given its simple formula, borane is a fundamental boron compound. It has attracted wide attention for its electronic structure. Several of its derivatives are useful reagents.

<span class="mw-page-title-main">Lithium aluminium hydride</span> Chemical compound

Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li[AlH4] or LiAlH4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters, carboxylic acids, and amides. The solid is dangerously reactive toward water, releasing gaseous hydrogen (H2). Some related derivatives have been discussed for hydrogen storage.

<span class="mw-page-title-main">Organolithium reagent</span> Chemical compounds containing C–Li bonds

In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers. They have also been applied in asymmetric synthesis in the pharmaceutical industry. Due to the large difference in electronegativity between the carbon atom and the lithium atom, the C−Li bond is highly ionic. Owing to the polar nature of the C−Li bond, organolithium reagents are good nucleophiles and strong bases. For laboratory organic synthesis, many organolithium reagents are commercially available in solution form. These reagents are highly reactive, and are sometimes pyrophoric.

<span class="mw-page-title-main">Sodium borohydride</span> Chemical compound

Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula NaBH4. It is a white crystalline solid, usually encountered as an aqueous basic solution. Sodium borohydride is a reducing agent that finds application in papermaking and dye industries. It is also used as a reagent in organic synthesis.

<span class="mw-page-title-main">Stibine</span> Chemical compound

Stibine (IUPAC name: stibane) is a chemical compound with the formula SbH3. A pnictogen hydride, this colourless, highly toxic gas is the principal covalent hydride of antimony, and a heavy analogue of ammonia. The molecule is pyramidal with H–Sb–H angles of 91.7° and Sb–H distances of 170.7 pm (1.707 Å). The smell of this compound from usual sources (like from reduction of antimony compounds) is reminiscent of arsine, i.e. garlic-like.

<span class="mw-page-title-main">Lithium hydride</span> Chemical compound

Lithium hydride is an inorganic compound with the formula LiH. This alkali metal hydride is a colorless solid, although commercial samples are grey. Characteristic of a salt-like (ionic) hydride, it has a high melting point, and it is not soluble but reactive with all protic organic solvents. It is soluble and nonreactive with certain molten salts such as lithium fluoride, lithium borohydride, and sodium hydride. With a molar mass of 7.95 g/mol, it is the lightest ionic compound.

<span class="mw-page-title-main">Germane</span> Chemical compound

Germane is the chemical compound with the formula GeH4, and the germanium analogue of methane. It is the simplest germanium hydride and one of the most useful compounds of germanium. Like the related compounds silane and methane, germane is tetrahedral. It burns in air to produce GeO2 and water. Germane is a group 14 hydride.

<span class="mw-page-title-main">Hydroperoxide</span> Class of chemical compounds

Hydroperoxides or peroxols are compounds of the form ROOH, where R stands for any group, typically organic, which contain the hydroperoxy functional group. Hydroperoxide also refers to the hydroperoxide anion and its salts, and the neutral hydroperoxyl radical (•OOH) consist of an unbond hydroperoxy group. When R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds.

<span class="mw-page-title-main">Sodium bis(2-methoxyethoxy)aluminium hydride</span> Chemical compound

Sodium bis(2-methoxyethoxy)aluminium hydride (SMEAH; trade names Red-Al, Synhydrid, Vitride) is a hydride reductant with the formula NaAlH2(OCH2CH2OCH3)2. The trade name Red-Al refers to its being a reducing aluminium compound. It is used predominantly as a reducing agent in organic synthesis. The compound features a tetrahedral aluminium center attached to two hydride and two alkoxide groups, the latter derived from 2-methoxyethanol. Commercial solutions are colorless/pale yellow and viscous. At low temperatures (below -60°C), the solution solidifies to a glassy pulverizable substance with no sharp melting point.

<span class="mw-page-title-main">Indium(III) chloride</span> Chemical compound

Indium(III) chloride is the chemical compound with the formula InCl3 which forms a tetrahydrate. This salt is a white, flaky solid with applications in organic synthesis as a Lewis acid. It is also the most available soluble derivative of indium. This is one of three known indium chlorides.

Hydrosilanes are tetravalent silicon compounds containing one or more Si-H bond. The parent hydrosilane is silane (SiH4). Commonly, hydrosilane refers to organosilicon derivatives. Examples include phenylsilane (PhSiH3) and triethoxysilane ((C2H5O)3SiH). Polymers and oligomers terminated with hydrosilanes are resins that are used to make useful materials like caulks.

<span class="mw-page-title-main">Digallane</span> Chemical compound

Digallane is an inorganic compound with the chemical formula GaH2(H)2GaH2. It is the dimer of the monomeric compound gallane. The eventual preparation of the pure compound, reported in 1989, was hailed as a "tour de force." Digallane had been reported as early as 1941 by Wiberg; however, this claim could not be verified by later work by Greenwood and others. This compound is a colorless gas that decomposes above 0 °C.

<span class="mw-page-title-main">Sodium aluminium hydride</span> Chemical compound

Sodium aluminium hydride or sodium alanate is an inorganic compound with the chemical formula NaAlH4. It is a white pyrophoric solid that dissolves in tetrahydrofuran (THF), but not in diethyl ether or hydrocarbons. It has been evaluated as an agent for the reversible storage of hydrogen and it is used as a reagent for the chemical synthesis of organic compounds. Similar to lithium aluminium hydride, it is a salt consisting of separated sodium cations and tetrahedral AlH−
4 anions.

<span class="mw-page-title-main">Beryllium hydride</span> Chemical compound

Beryllium hydride is an inorganic compound with the chemical formula n. This alkaline earth hydride is a colourless solid that is insoluble in solvents that do not decompose it. Unlike the ionically bonded hydrides of the heavier Group 2 elements, beryllium hydride is covalently bonded.

<span class="mw-page-title-main">Magnesium hydride</span> Chemical compound

Magnesium hydride is the chemical compound with the molecular formula MgH2. It contains 7.66% by weight of hydrogen and has been studied as a potential hydrogen storage medium.

Zinc hydride is an inorganic compound with the chemical formula ZnH2. It is a white, odourless solid which slowly decomposes into its elements at room temperature; despite this it is the most stable of the binary first row transition metal hydrides. A variety of coordination compounds containing Zn–H bonds are used as reducing agents, but ZnH2 itself has no common applications.

Zirconocene dichloride is an organozirconium compound composed of a zirconium central atom, with two cyclopentadienyl and two chloro ligands. It is a colourless diamagnetic solid that is somewhat stable in air.

<span class="mw-page-title-main">Carbonyl reduction</span> Organic reduction of any carbonyl group by a reducing agent

In organic chemistry, carbonyl reduction is the conversion of any carbonyl group, usually to an alcohol. It is a common transformation that is practiced in many ways. Ketones, aldehydes, carboxylic acids, esters, amides, and acid halides - some of the most pervasive functional groups, -comprise carbonyl compounds. Carboxylic acids, esters, and acid halides can be reduced to either aldehydes or a step further to primary alcohols, depending on the strength of the reducing agent. Aldehydes and ketones can be reduced respectively to primary and secondary alcohols. In deoxygenation, the alcohol group can be further reduced and removed altogether by replacement with H.

<span class="mw-page-title-main">Copper hydride</span> Chemical compound

Copper hydride is an inorganic compound with the chemical formula CuHn where n ~ 0.95. It is a red solid, rarely isolated as a pure composition, that decomposes to the elements. Copper hydride is mainly produced as a reducing agent in organic synthesis and as a precursor to various catalysts.

References

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