Di(2-ethylhexyl)phosphoric acid

Names
Preferred IUPAC name

Bis(2-ethylhexyl) hydrogen phosphate

Other names

Bis(2-ethylhexyl) phosphoric acid
Bis(2-ethylhexyl) phosphate
Bis(2-ethylhexyl) hydrophosphoric acid
BEHPA
BEHP
BEHHPA
BEHHP
Di(2-ethylhexyl) phosphoric acid
DEHPA
D2EHPA
EHPA

Identifiers

CAS Number

* 298-07-7 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 8918 N

PubChem CID

* 9275

UNII |

* 2Z4W0L3H06 Y

InChI

* InChI=1S/C16H35O4P/c1-5-9-11-15(7-3)13-19-21(17,18)20-14-16(8-4)12-10-6-2/h15-16H,5-14H2,1-4H3,(H,17,18) N

Key: SEGLCEQVOFDUPX-UHFFFAOYSA-N N

* InChI=1/C16H35O4P/c1-5-9-11-15(7-3)13-19-21(17,18)20-14-16(8-4)12-10-6-2/h15-16H,5-14H2,1-4H3,(H,17,18)

Key: SEGLCEQVOFDUPX-UHFFFAOYAP

SMILES

* CCCCC(CC)COP(=O)(O)OCC(CC)CCCC

Properties

Chemical formula

| C16H35O4P
Molar mass | 322.43 g/mol
Appearance  | odorless colorless liquid (impure samples are often yellow)
Density | 0.9758 g/mL
Melting point |  −50 °C (−58 °F; 223 K)
Boiling point |  393 °C (739 °F; 666 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Di(2-ethylhexyl)phosphoric acid (DEHPA or HDEHP) is an organophosphorus compound with the formula (C8H17O)2PO2H. The colorless liquid is a diester of phosphoric acid and 2-ethylhexanol. It is used in the solvent extraction of uranium, vanadium and the rare-earth metals.[1]

## Contents

* 1 Preparation
* 2 Use in Lanthanide extraction
* 3 Use in uranium extraction
* 3.1 Extraction
* 3.2 Stripping
* 3.3 Synergistic effects
* 3.4 Alternatives to DEHPA
* 4 References

## Preparation

DEHPA is prepared through the reaction of phosphorus pentoxide and 2-ethylhexanol:

4 C8H17OH + P4O10 → 2 [(C8H17O)PO(OH)]2O
[(C8H17O)PO(OH)]2O + C8H17OH → (C8H17O)2PO(OH) + (C8H17O)PO(OH)2

These reaction produce a mixture of mono-, di-, and trisubstituted phosphates, from which DEHPA can be isolated based on solubility.[2]

## Use in Lanthanide extraction

DEHPA can be used to extract lanthanides (rare earths) from aqeuous solutions, it is commonly used in the lanthanide sector as an extraction agent. In general the distribution ratio of the lanthanides increase as their atomic number increaases due to the lanthanide contraction. It is possible by bringing a mixture of lanthanides in a counter current mixer settler bank into contact with a suitable concentration of nitric acid to selectively strip (back extract) some of the lanthanides while leaving the others still in the DEHPA based organic layer.[3] In this way selective stripping of the lanthanides can be used to make a separation of a mixture of the lanthanides into mixtures containing fewer lanthanides. Under ideal conditions this can be used to obtain a single lanthanide from a mixture of many lanthanides.

It is common to use DEHPA in an aliphatic kerosene which is best considered to be a mixture of long chain alkanes and cycloalkanes. When used in an aromatic hydrocarbon diluent the lanthanide distribution ratios are lower. It has been shown that it is possible to use a second generation biodiesel which was made by the hydrotreatment of vegtable oil. It has been reported that Neste's HVO100 is a suitable diluent for DEHPA when calcium, lanthanum and neodynium are extracted from aqueous nitric acid[4]

## Use in uranium extraction

### Extraction

DEHPA is used in the solvent extraction of uranium salts from solutions containing the sulfate, chloride, or perchlorate anions. This extraction is known as the “Dapex procedure” (dialkyl phosphoric extraction). Reminiscent of the behaviours of carboxylic acids, DEHPA generally exists as a hydrogen-bonded dimer in the non-polar organic solvents. For practical applications, the solvent, often called a diluent, is typically kerosene.[5] A complex is formed from two equivalents of the conjugate base of DEHPA and one uranyl ion.[6] Complexes of the formula (UO2)2[(O2P(OR)2]4 also form, and at high concentrations of uranium, polymeric complexes may form.[5]

The extractability of Fe3+ is similar to that of uranium, so it must be reduced to Fe2+ before the extraction.[5]

### Stripping

The uranium is then stripped from the DEHPA/kerosene solution with hydrochloric acid, hydrofluoric acid, or carbonate solutions. Sodium carbonate solutions effectively strip uranium from the organic layer, but the sodium salt of DEHPA is somewhat soluble in water, which can lead to loss of the extractant.[2]

### Synergistic effects

The extractive capabilities of DEHPA can be increased through synergistic effects by the addition of other organophosphorus compounds. Tributyl phosphate is often used, as well as dibutyl-, diamyl-, and dihexylphosphonates. The synergistic effects are thought to occur by the addition of the trialkylphosphate to the uranyl-DEHPA complex by hydrogen bonding. The synergistic additive may also react with the DEHPA, competing with the uranyl extraction, resulting in a decrease in extraction efficiency past a concentration specific to the compound. [7]

### Alternatives to DEHPA

Alternative organophosphorus compounds include trioctylphosphine oxide and bis(2,4,4-trimethyl pentyl)phosphinic acid.[8] Secondary, tertiary, and quaternary amines have also been used for some uranium extractions. Compared to phosphate extractants, amines are more selective for uranium, extract the uranium faster, and are easily stripped with a wider variety of reagents. However, the phosphates are more tolerant of solids in the feed solution and show faster phase separation.[7]

## References

1. ↑ Sato, T. Hydrometallurgy, 1989, volume 22, 121–140. doi:10.1016/0304-386X(89)90045-5
2. ↑ 2.0 2.1 Galkin, N.P.; Sudarikov, B.N.; Veryatin, U.D.; Shishkov, Yu.D.; Maiorov, A.A. Technology of Uranium, 1st Ed.; Israel Program for Scientific Translations: Jerusalem, 1966.
3. ↑ Li Chen, Hailian Li, Ji Chen, Deqian Li, Tianchi Liu, Minerals Engineering, 2020, volume 149, 106232
4. ↑ Mark R. StJ. Foreman, Richard K. Johansson, Gloria Mariotti, Ingmar Persson, Behabitu E. Tebikachew, Mikhail S. Tyumentsev, RSC Sustainability, January 2024, Sustainable solvent extraction of gold and other metals with biomass chemicals, DOI 10.1039/d3su00078h
5. ↑ 5.0 5.1 5.2 Wilkinson, W.D. Uranium Metallurgy, 1st Ed.; Interscience Publishers: New York, 1962; Vol. 1.
6. ↑ Lemire, A.E.; Janzen, A.F.; Marat, K. A 31P and 15N Study of the Extraction of Uranyl Nitrate by Di-2-ethylhexyl Phosphoric Acid. Inorg. Chim. Acta, 1985, 110, 234-241. doi:10.1016/S0020-1693(00)82312-9
7. ↑ 7.0 7.1 Merritt, R.C. The Extractive Metallurgy of Uranium, 1st Ed.; Colorado School of Mines Research Institution, 1971.
8. ↑ Kumar, Jyothi Rajesh; Kim, Joon-Soo; Lee, Jin-Young; Yoon, Ho-Sung (18 February 2011). "A Brief Review on Solvent Extraction of Uranium from Acidic Solutions". Separation & Purification Reviews 40 (2): 77–125. doi:10.1080/15422119.2010.549760.

* v
* t
* e

Separation processes

Processes|

* Absorption
* Acid-base extraction
* Adsorption
* Chromatography
* Cross-flow filtration
* Crystallization
* Cyclonic separation
* Dialysis (biochemistry)
* Dissolved air flotation
* Distillation
* Drying
* Electrochromatography
* Electrofiltration
* Filtration
* Flocculation
* Froth flotation
* Gravity separation
* Leaching
* Liquid–liquid extraction
* Electroextraction
* Microfiltration
* Osmosis
* Precipitation (chemistry)
* Recrystallization
* Reverse osmosis
* Sedimentation
* Solid phase extraction
* Sublimation
* Ultrafiltration

Devices|

* API oil-water separator
* Belt filter
* Centrifuge
* Depth filter
* Electrostatic precipitator
* Evaporator
* Filter press
* Fractionating column
* Leachate
* Mixer-settler
* Protein skimmer
* Rapid sand filter
* Rotary vacuum-drum filter
* Scrubber
* Spinning cone
* Still
* Sublimation apparatus
* Vacuum ceramic filter

Multiphase
systems|

* Aqueous two-phase system
* Azeotrope
* Eutectic

Concepts|

* Unit operation

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