Aluminium phenolate

Names
Other names

Aluminium phenoxide

Identifiers

CAS Number

* 15086-27-8

3D model (JSmol)

* Interactive image

ChemSpider |

* 146313

EC Number |

* 239-137-8

PubChem CID

* 167236

InChI

* InChI=1S/3C6H6O.Al/c3*7-6-4-2-1-3-5-6;/h3*1-5,7H;/q;;;+3/p-3

Key: OPSWAWSNPREEFQ-UHFFFAOYSA-K

SMILES

* C1=CC=C(C=C1)[O-].C1=CC=C(C=C1)[O-].C1=CC=C(C=C1)[O-].[Al+3]

Properties

Chemical formula

| C18H15AlO3
Molar mass | 306.297 g·mol−1
Appearance  | white solid
Hazards
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H314

GHS precautionary statements

| P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P405, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Aluminium phenolate is the metalloorganic compound with the formula [Al(OC6H5)3]n. It is a white solid. 27Al NMR studies suggest that aluminium phenolate exists in benzene solution as a mixture of dimer and trimer.[2] The compound can be prepared by the reaction of elemental aluminium with phenol:[3]

Al + 3 HOC6H5 → Al(OC6H5)3 \+ 1.5 H2

The compound is used as a catalyst for the alkylation of phenols with various alkenes. For example, the ethylphenols are generated commercially by treating phenol with ethylene in the presence of a catalytic amount of aluminium phenolate.[4]

## Related compounds

* Aluminium isopropoxide

## References

1. ↑ "Aluminium triphenolate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/167236#section=Safety-and-Hazards.
2. ↑ Kříž, O.; Čásenský, B.; Lyčka, A.; Fusek, J.; Heřmánek, S. (1984). "27Al NMR Behavior of Aluminum Alkoxides". Journal of Magnetic Resonance 60 (3): 375–381. doi:10.1016/0022-2364(84)90048-9. Bibcode: 1984JMagR..60..375K.
3. ↑ Kolka, Alfred J.; Napolitano, John P.; Filbey, Allen H.; Ecke, George G. (1957). "The ortho-Alkylation of Phenols". The Journal of Organic Chemistry 22 (6): 644. doi:10.1021/jo01357a014. "The aluminum phenoxide catalyst was prepared by adding 4.5 g. (​1⁄6 formula wt.) of aluminum turnings in small amounts and with vigorous stirring to 300 g. of phenol at 165° under a nitrogen atmosphere.".
4. ↑ Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef et al. (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. p. 533. doi:10.1002/14356007.a19_313.

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*[CID]: Compound ID
*[H314]: Causes severe skin burns and eye damage
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P301+330+331]: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P321]: Specific treatment (see … on this label)
*[P363]: Wash contaminated clothing before reuse
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …