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Tetrabutylammonium dodecatungstophosphate

  1. Mark B. Anderson

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rn01585

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Anderson, M. B. 2013. Tetrabutylammonium dodecatungstophosphate. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. Biotech Pharma Solutions, Orinda, CA, USA

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

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Abstract

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[53749-37-4] C48H108N3O40PW12 MW = 3604.44

(early transition metal oxidation catalysts for the oxidation of organic substrates; examples include cyclooctane, cyclooctene, cyclohexene, pentan-2-ol, 4-methylpentan-2-ol, cyclohexanol, octan-2-ol, 1-phenylethanol, and isobutyraldehyde)

Alternate Names: Keggin-type POM; tris(tetrabutylammonium) 12-tungstophosphate; 1-butanaminium, N,N,N-tributyl-, tetracosa-m-oxododecaoxo[m12-(phosphato(3−)-kO:kO:kO:kO′:kO′:kO′:kO″:kO″:kO″:kO‴:kO‴:kO‴)]dodecatungstate(3−) (3:1); tungstate(3−),tetracosa-m-oxododecaoxo[m12-(phosphato(3−)- kO:kO:kO:kO′:kO′:kO′:kO″:kO″:kO″:kO‴:kO‴:kO‴)]dodeca-,tris(N,N,N-tributyl-1-butanaminium) or tetra-n-butylammonium12-tungstophosphate.

Physical Data: chemical formula: C16H36N·1/3O40PW12; white solid; α-Keggin structures are stable and self-assemble in acidic aqueous solution; the ammonium salt is stable solid at room temperature but may decompose at elevated temperatures; for comparison 12-tungstophosphoric acid is thermally stable up to 400 °C.

Solubility: (TBA)3[PW12O40] is soluble in acetonitrile, dichloromethane, acetic acid, and ionic liquids; for comparison 12-tungstophosphoric acid [1343-93-7](H3PW12O40) and the 12-tungstophosphoric acid hydrate [12501-23-4] are water soluble.

Form Supplied in: not commercially available.

Analysis of Reagent Purity: pure reagents show a characteristic isolated signal by 31P-NMR for the PW12 Keggin structure in DMF at − 14.5 ppm (singlet). Reagents containing the PW4 species, or PW4 intermediates, show a characteristic signal by 31P-NMR in DMF at 0.53 ppm (singlet). UV-Vis shows a characteristic absorption peak2 for the PW12 species [PW12O40]3− near 260 nm.

Preparative Methods: a solution of 12-tungstophospholic acid (1.5 mmol) in distilled water (20 mL) was added dropwise to a solution of the tetrabutylammonium chloride (4.5 mmol) in distilled water (80 mL) with vigorous stirring. The white precipitate (TBA)3[PW12O40] appears immediately and the suspension is stirred for 1 h. The white precipitate is filtered, washed 2× with distilled water, and dried under low pressure for 24 h. Numerous reagents can be prepared in this manner using a variety of alkyl ammonium salts. A similar procedure was used to prepare several additional ammonium and guanidinium salt forms including the tetra-n-butylammonium version discussed in this article.3

Purification: The ammonium salt is sparingly soluble in water and is of high purity when prepared under the method described above.

Handling, Storage, and Precautions: stable to air and moisture; decomposition in the presence of excess H2O2 (aq.); full toxicity studies have not been performed; skin/eye contact and inhalation should be avoided.

Featured Compounds

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Compound Information
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:URYYVOIYTNXXBN-UPHRSURJSA-N
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:MELPJGOMEMRMPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:34.0147
Molecular Formula:H2O2
InChIKey:MHAJPDPJQMAIIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:3604.42
Molecular Formula:C48H108N3O40PW12
InChIKey:PUEMLSFWZAUDPQ-UHFFFAOYSA-K
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Compound Information
Molecular Weight:130.2279
Molecular Formula:C8H18O
InChIKey:Not Available
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:ZPVFWPFBNIEHGJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.2126
Molecular Formula:C8H16
InChIKey:WJTCGQSWYFHTAC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:FHADSMKORVFYOS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:IIRFCWANHMSDCG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.2114
Molecular Formula:C8H16O2
InChIKey:DTMZBUVZQPKYDT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:41.0519
Molecular Formula:C2H3N
InChIKey:WEVYAHXRMPXWCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:AMIMRNSIRUDHCM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:KQNPFQTWMSNSAP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.2126
Molecular Formula:C8H16
InChIKey:KWKAKUADMBZCLK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:Not Available
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Compound Information
Molecular Weight:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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