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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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50 G
€142.00

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5 G
€30.40
50 G
€142.00

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

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Quality Level

100

Assay

≥90.0%

impurities

≤1.0% water

density

0.895 g/mL at 20 °C (lit.)

functional group

phosphine

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

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General description

Trihexyltetradecylphosphonium bis(2,4,4-trimethylpentyl)phosphinate is a phosphonium-based ionic liquid.[1] It can be prepared by reacting trihexyl(tetradecyl)-phosphonium chloride with bis(2,4,4-trimethylpentyl)phosphinic acid in the presence of a base.[2]
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).[3]

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

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL3980
BCCJ8065
BCCH3358
BCCJ2839
BCCD6791

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Proazaphosphatranes: Superior bases and catalysts
Aldrichimica Acta, 37(1), 32-32 (2004)
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)
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)
Phosphonium-based ionic liquids: An overview
Fraser, Kevin J., and Douglas R. MacFarlane
Australian Journal of Chemistry, 62.4, 309-321 (2009)
Phosphonium ionic liquids as new, reactive extractants of lactic acid
Martak, J., and S. Schlosser
Chemical Papers, 60.5, 395-398 (2006)
View All Related Papers

Questions

  1. Trihexyltetradecylphosphonium bis(2,4,4-trimethylpentyl)phosphinate is this compound applicable in metal separation (solvent extraction). I am interested in separation of transition metals and lanthanides.

    1 answer

    1. This product, as well as other phosphonium-based ionic liquids offered, have not been tested for suitability in the separation of lanthanides. Please see the links below for information that may be helpful.
      Solvent Extraction and Separation of Trivalent Lanthanides Using Cyphos IL 104, a Novel Phosphonium Ionic Liquid as Extractant
      https://www.tandfonline.com/doi/abs/10.1080/07366299.2016.1207459

      Speciation of lanthanide ions in the organic phase after extraction from nitrate media by basic extractants
      https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6333249/

      Helpful?

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