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Sigma-Aldrich

Trihexyltetradecylphosphonium bis(2,4,4-trimethylpentyl)phosphinate

≥90.0%

Synonym(s):

Tetradecyltrihexylphosphonium bis(2,4,4-trimethylpentyl)phosphinate

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About This Item

Empirical Formula (Hill Notation):
C48H102O2P2
CAS Number:
465527-59-7
Molecular Weight:
773.27
MDL number:
MFCD04117696
UNSPSC Code:
12352100
PubChem Substance ID:
57648314
NACRES:
NA.22

assay

≥90.0%

impurities

≤1.0% water

density

0.895 g/mL at 20 °C (lit.)

SMILES string

CC(CC(C)(C)C)CP([O-])(=O)CC(C)CC(C)(C)C.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC

InChI

1S/C32H68P.C16H35O2P/c1-5-9-13-17-18-19-20-21-22-23-24-28-32-33(29-25-14-10-6-2,30-26-15-11-7-3)31-27-16-12-8-4;1-13(9-15(3,4)5)11-19(17,18)12-14(2)10-16(6,7)8/h5-32H2,1-4H3;13-14H,9-12H2,1-8H3,(H,17,18)/q+1;/p-1

InChI key

ZKQLVOZSJHOZBL-UHFFFAOYSA-M

General description

Trihexyltetradecylphosphonium bis(2,4,4-trimethylpentyl)phosphinate is a phosphonium-based ionic liquid. It can be prepared by reacting trihexyl(tetradecyl)-phosphonium chloride with bis(2,4,4-trimethylpentyl)phosphinic acid in the presence of a base.
http://www.sigmaaldrich.com/dam/sigma-aldrich/docs/Aldrich/Acta/al_acta_37_1.pdf

Application

It can be used as an extractant for the removal of dibenzothiophene from liquid fuels via extractive desulfurization (EDS).

Features and Benefits

Phosphonium-based ionic liquid possess interesting properties such as:
  • Liquid at room temperature or melting at T <100 °C
  • High thermal stability
  • Immiscible with water
  • Soluble in organic solvents (however, when an excess of water is added to the system, three liquid phases are formed)
  • Stable under basic conditions

Other Notes

A phosphonium phosphinate for use as a polar solvent

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Unusual trend of viscosities and densities for four ionic liquids containing a tetraalkyl phosphonium cation and the anion bis (2, 4, 4-trimethylpentyl) phosphinate
Liu, Xiangyang, Waheed Afzal, and John M. Prausnitz
The Journal of Chemical Thermodynamics, 70, 122-126 (2014)
Phosphonium-based ionic liquids: An overview
Fraser, Kevin J., and Douglas R. MacFarlane
Australian Journal of Chemistry, 62.4, 309-321 (2009)
Separation of rare earths and nickel by solvent extraction with two mutually immiscible ionic liquids
Rout, Alok, Sil Wellens, and Koen Binnemans
Royal Society of Chemistry Advances, 4.11, 5753-5758 (2014)
Proazaphosphatranes: Superior bases and catalysts
Aldrichimica Acta, 37(1), 32-32 (2004)
Electrochemical reactivity of trihexyl (tetradecyl) phosphonium bis (2, 4, 4-trimethylpentyl) phosphinate ionic liquid on glassy carbon and AZ31 magnesium alloy
Latham, Julie-Anne, et al.
Electrochimica Acta, 56.15, 5328-5334 (2011)
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