Aluminium phenolate
Names
Other names
Aluminium phenoxide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.035.565
EC Number
  • 239-137-8
  • 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
  • C1=CC=C(C=C1)[O-].C1=CC=C(C=C1)[O-].C1=CC=C(C=C1)[O-].[Al+3]
Properties
C18H15AlO3
Molar mass 306.297 g·mol−1
Appearance white solid
Hazards
GHS labelling:[1]
GHS05: Corrosive
Danger
H314
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, 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 is 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]

References

  1. ↑ "Aluminium triphenolate". pubchem.ncbi.nlm.nih.gov.
  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. Bibcode:1984JMagR..60..375K. doi:10.1016/0022-2364(84)90048-9.
  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): 642–646. doi:10.1021/jo01357a014.
  4. ↑ Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3527306732.
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