Aluminium phenolate

Aluminium phenolate
Names
	Other names Aluminium phenoxide
Identifiers
CAS Number	15086-27-8;
3D model (JSmol)	Interactive image;
ChemSpider	146313;
ECHA InfoCard	100.035.565
EC Number	239-137-8;
PubChem CID	167236;
CompTox Dashboard (EPA)	DTXSID401015343 ;
	InChI InChI=1S/3C6H6O.Al/c37-6-4-2-1-3-5-6;/h31-5,7H;/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 labelling:
Pictograms
Signal word	Danger
Hazard statements	H314
Precautionary statements	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]

Related compounds

Aluminium isopropoxide

References

^ "Aluminium triphenolate". pubchem.ncbi.nlm.nih.gov.
^ 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.
^ 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.
^ Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. p. 533. doi:10.1002/14356007.a19_313. ISBN 3527306730. 2‑Ethylphenol and 2,6‑diethylphenol are produced industrially by ortho-alkylation of phenol with ethylene in high pressure autoclaves at 320‑340 °C and 20 MPa in the presence of 1‑2% aluminum phenolate.

[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): 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; Garbe, Dorothea; Paulus, Wilfried (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. p. 533. doi:10.1002/14356007.a19_313. ISBN 3527306730. 2‑Ethylphenol and 2,6‑diethylphenol are produced industrially by ortho-alkylation of phenol with ethylene in high pressure autoclaves at 320‑340 °C and 20 MPa in the presence of 1‑2% aluminum phenolate.

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