Part I Chapter 2: Introduction to Cyanex

2.1 Introduction to cyanex compounds

Cyanex extractants are organophosphorous compounds. Depending on their
chemical compositions and structural properties there are different types of
cyanex compounds such as, cyanex 921, cyanex 272, cyanex 301, cyanex 923,
cyanex 471X, cyanex 302, cyanex 925 etc. Cyanex extractants are phosphorusbased products that act in two different ways:
a) Chelating Extractants
b) Solvating Extractants

a) Chelating Extractants
Cyanex 272 solvent extraction reagent was developed specifically for the
separation of cobalt from nickel by solvent extraction. It is estimated that 40%
of the cobalt in the western hemisphere is produced using cyanex 272 solvent
extraction reagent, at plants Europe, South America , Canada , Africa, China
and Australia. Cyanex 272 solvent extraction reagent can also be used to
separate the rare earth elements from one another. The acid concentration
required for metal stripping is lower than when phosphoric acid or phosphonic
acid are used as extractants. Cyanex 301 solvent extraction reagent is an
analogue of cyanex 272 solvent extraction reagent. Thiophosphinic acid cyanex
301 solvent extraction reagent exhibits interesting extraction characteristics for
the recovery of cobalt and nickel. A potential advantage of the dithiophosphinic
acid cyanex 301 over cyanex 272 is its ability to extract both cobalt and nickel
under very acidic conditions avoiding therefore the need for pH adjustment of
the acidic leach liquors.

b) Solvating Extractants
Cyanex 921 and 923 solvent extraction reagents have potential in a wide
range of applications. Specific applications are the recovery of organic solutes
and inorganic mineral acids from waste effluents, and metal extraction
processes. Unlike its phosphine oxide analogues, cyanex 471X solvent
extraction reagent is a soft Lewis base. Under the HSAB principle, it will only

13

Part I Chapter 2: Introduction to Cyanex

complex readily with metals that exhibit the characteristics of soft Lewis acids.
Specific characteristics of these so-called soft Lewis acids are their large ionic
radius, their low oxidation state and their ease to be polarized. Examples of
metals falling upon those criteria are Pd(II), Pt(II), Ag(I), Cd(II), Hg(I), Hg (II)
and Au(III).
The cyanex compounds are very useful and effective in case of solvent
extraction of metal ions. Now a days these cyanex compounds are widely used
extractants for separation of metal ions. The detailed information of some of
the cyanex compounds are described [1].

14

Part I Chapter 2: Introduction to Cyanex

2.2 Properties of cyanex compounds

The properties of different cyanex compounds are shown in Table 2.2.
Table 2.2 Properties of different cyanex compounds

Name of
cyanex
Properties

Cyanex
921

Cyanex 272

Cyanex
923

Cyanex
301

Cyanex
471X

% Purity
93
Appearance Off-white,
waxy
solid
Molecular
386
Weight
Specific
0.88 at 25
0
gravity
C
Viscosity
150 cp

85
colourless to
light amber
liquid
290

93
colourless
mobile
liquid

75-80
Green
mobile
liquid
322

Off-white
crystalline
solid

0.92 at 24 0C

Solubility
In Distilled
water
Boiling
point
Pour point
Flash point

16g/mL at
pH 2.6

0.88 at 25
0
C
40 cp at 25
0
C
10 mg/L

0.95 at 24
0
C
78 cp at
24 0C
7 mg/L

310 0C at
50 mm Hg

220 0C

>300 0C
-32 0C
>108
0
C(closed
cup)

Specific
heat
Thermal
conductivit
y
Melting
point

37 cp

0.48
cal/gm/0C at
25 0C
2.7x 10-4
cal/cm/sec./0
C
47-52 0C

182 0C
(Closed
cup
setaflash)
0.45
cal/gm/0C
at 25 0C
0.000302
cal/cm/sec.
/ 0C

0.91 at 22
0
C

43g/mL
at 240C

-34 0C
74 0C
(closed
cup)

58-59 0C

15

Part I Chapter 2: Introduction to Cyanex

2.3 Cyanex 921 extractant

Cyanex 921 is commonly known as trioctylphosphine oxide (TOPO). It was the
first member of a family of solvent extraction reagents developed by Cytec.
This reagent has been used commercially for many years to recover uranium
from wet process phosphoric acid. It is also used in the extraction of different
metals.

2.3.1 Chemical Structure of cyanex 921

The chemical structure of cyanex 921 is as follows:

O
CH3(CH2)7-P-(CH2)7CH3
(CH2)7CH3
2.3.2 Stability of cyanex 921
Among trialkylphosphine oxides, cyanex 921 is most stable member of
the group of organophosphorous solvating reagents.

2.3.3 Organic solubility of cyanex 921

The solubility of cyanex 921 is higher in aromatic diluents than the
aliphatic ones.

2.3.4 Toxicity of cyanex 921

The acute oral and acute dermal LD50 values for cyanex 921 extractant
are > 10.0 g/ kg and 2.83 g/ kg, respectively. Marked skin and eye irritation
were produced during primary irritation studies with rabbits. Inhalation of
airborne material may be irritating to the respiratory tract. Cyanex 921 was
determined to be not mutagenic in the Ames Salmonella Assay.

16

Part I Chapter 2: Introduction to Cyanex

2.3.5 Applications of Cyanex 921

Cyanex 921 is a better extractant because of its higher stability, lower
aqueous solubility and rapid phase engagement. There are numerous
applications of cyanex 921.
1. The solvent extraction method was developed to recover small quqntities of
uranium present in wet process phosphoric acid using cyanex 921.
2. Processes in petrochemical plants, wood pulp mills and other chemical
facilities

often

generate

aqueous

effluent

streams

containing

small

concentrations of carboxylic acids; particularly acetic acid. The use of cyanex

921 and others reagents to recover acetic acid from these streams has formed
the subject of informative papers in recent years.
3. Cyanex 921 is used to extract niobium and tantalum from a hydrofluoricsulphuric acid leach liquor and then selectively stripped from the loaded
organic phase.
4. Rhenium is an essential element in the production of petroleum reforming
catalysts. Cyanex 921 was used to recover rhenium from these source
materials.
5. Removal of arsenic impurities from copper electrolytes by solvent extraction
with cyanex 921 was carried out. It was found that cyanex 921 is stronger
extractant for arsenic than tributylphosphate.
6. Because of wide applications of lithium in batteries and ceramics a novel
solvent extraction process using cyanex 921 extractant to recover lithium from
its sources was developed.
7. Selective separations can be made depending upon a variety of factors, e.g.
the valence state of metal, the anionic nature of the solution and the
concentration of the extractant in the solvent. Approximately 30 metals were
known to be extracted by cyanex 921.
8. Phenol occurs in aqueous effluent from many processes such as, in the
petroleum, steel and coal gasification industries. Cyanex 921 is a strong
extractant for phenol recovery and offers a lower cost alternative to
conventional phenosolvan technology.

17

Part I Chapter 2: Introduction to Cyanex

2.4 Cyanex 272 Extractant

Bis(2,4,4- trimethylpentyl)phosphinic acid commonly known as cyanex
272. The active component of cyanex 272 extractant is a phosphoric acid;
metals are extracted through a cation exchange mechanism. Though cyanex
272 is a selective extractant for cobolt in the presence of nickel, a variety of
other cations can be extracted depending upon the solution pH.

2.4.1 Chemical Structure of cyanex 272

The chemical structure of cyanex 272 is as follows
CH3

CH3

CH3-C-CH2-CH-CH2
CH3

O
P

CH3

OH

CH3-C-CH2-CH-CH2
CH3

CH3

2.4.2 Stability of cyanex 272

The hydrophilic stability of cyanex 272 extractant was examined in several
tests and it was found that cyanex 272 is having highest stability.

2.4.3 Organic solubility of cyanex 272

Cyanex 272 extractant is totally miscible with common aromatic and
aliphatic diluents, and is extremely stable to both heat and hydrolysis.

2.4.4 Toxicity of cyanex 272

The acute oral and acute dermal LD50 values for cyanex 272 extractant
are > 3.5 g/ kg and 2.0 g/ kg, respectively. It is limited to skin and eye irritation
during primary irritation studies with rabbits. Cyanex 272 was determined to be
non-mutagenic in the Ames Salmonella Assay.

18

Part I Chapter 2: Introduction to Cyanex

2.4.5 Applications of Cyanex 272

1. Cyanex 272 is used as a selectve extractant for the extraction and separation
of cobalt in the presence of nickel.
2. Cyanex 272 is found to be preferentially selective extractant for cobalt in the
presence of calcium.
3. Cyanex 272 can be used to recover cobalt from ammoniacal as well as acidic
solutions.
4. Using cyanex 272 metals like iron, zinc. Copper, manganese, calcium, nickel
from sulphate solutions can be extracted.

2.5 Cyanex 923 Extractant

Cyanex 923 extractant is a liquid phosphine oxide which has potential
applications in the solvent extraction recovery of both organic and inorganic
solutes from aqueous solution, e.g. carboxylic acids from effluent streams and
the removal of arsenic impurities from copper electrolytes.

2.5.1 Compositions of cyanex 923

Cyanex 923 extractant is a mixture of four trialkyl-phosphine oxides as
follows:
(1) Trihexylphosphine oxide (2) dihexylmonooctyl-phosphine oxide
(3) dioctylmonohexyl-phosphine oxide (4) Trioctylphosphine oxide.
R3P(O)

R2RP(O)

RR2P(O)

R3P(O)

Where, R= [CH3(CH2)7]-normal octyl

R = [CH3(CH2)7]-normal octyl
2.5.2 Organic solubility of cyanex 923
Cyanex 923 extractants are completely miscible with all common
hydrocarbon diluents even at very low ambient temperatures. The major benefit
of high solubility lies the ability to prepare concentrated, stable solvents which
can recover solutes (e.g. acetic acid) that are normally only weakly extracted by
this type of reagent.

19

Part I Chapter 2: Introduction to Cyanex

2.5.3 Applications of Cyanex 923

1.

Processes in petrochemical plants, wood pulping mills, and other

chemical facilities often generate aqueous effluent streams containing
carboxylic acids: particularly acetic acid. These carboxylic acids are
recovered by cyanex 923.

2.

Phenols, like carboxylic acids are produced during coal liquefaction, coal
gasification and in the petrochemical industry and they can be efficiently
extracted by cyanex 923.

3.

Cyanex 923 extractant exhibits a separation factor in ethanol/water

solutions near the maximum useful limit for recovery from continuous
fermentation broths, typically containing 5% ethanol.

4.

Removing arsenic, antimony and bismuth impurities from copper

electrolytes by solvent extraction with cyanex 923 improves the quality
of electrolytic copper and consists of improvements in current efficiency.

5.

Uranium recovery from wet-process phosphoric acid using synergic

mixtures of phosphine oxides and D2EHPA.

6.

Niobium and tantalum are extracted and separated by cyanex 923.

7.

Cadmium sometimes occurs as an undesirable impurity in phosphoric

acid and other acids can be removed by cyanex 923.

2.6 Cyanex 301 extractant

Cyanex 301 is a dialkyl dithiophosphinic acid extractant. This sulphur
containing compound is a much stronger acid than its analogous oxy-acid,
cyanex 272. It is capable of extracting many metals at lower pH (<2). Cyanex
301 extractant does not discriminate between heavy metals in this pH range,
however, a high degree of selectivity of extraction of heavy metals vs the
alkaline earths is observed.

2.6.1Chemical structure of cyanex 301

The chemical structure of cyanex 301 is as follows

20

Part I Chapter 2: Introduction to Cyanex

R

S
P
SH

Where,

CH3
R=CH3-C-CH2-CH-CH2CH3

CH3

The active component of cyanex 301 is bis(2,4,4-trimethylpentyl)

dithiophosphinic acid.

2.6.2 Applications of cyanex 301

Cyanex 301 extractant is capable of the selective recovery of heavy
metals at low pH in the presence of alkaline earths.
1. Cadmium from wet process phosphoric acid and amino acids from
fermentation broths were capable to extract by cyanex 301.
2. Cyanex 301 was developed to extract and recover zinc from the effluent
streams of viscose rayon plants in the presence of calcium.
3. Dialkyl dithiophoshinic acids, or their salts, have shown to be effective in
extracting a number of alpha amino acids from fermentation broths. The
recovery of L-phenylalanine was done using cyanex 301 extractant.

2.7 Cyanex 471X extractant

Cyanex 471X extractant is a new phosphine based extractant developed
by Cyanamid for the hydrometallurgical industry. It is particularly useful for
the selective recovery of silver and in the separation of palladium from
platinum.

2.7.1 Chemical Structure of cyanex 471X

The chemical structure of cyanex 471X is as follows

21

Part I Chapter 2: Introduction to Cyanex

CH3-CH2-CH2
CH3

P=S
3

2.7.2 Toxicity of cyanex 471X

The acute oral (rat) and acute dermal (rabbit) LD50 values for the active
phosphine sulphide contained in cyanex 471X extractant are 10,000 mg/kg of
body weight. No significant skin irritation and only mild eye irritation were
produced during primary irritation studies with rabbits. The sulfide was
determined to be non-mutagenic in the Ames Salmonella Assay.

2.7.3 Applications of cyanex 471X

1. Cyanex 471X is a solvating reagent and will extract silver from sulfate,
nitrate and chloride systems.
2. Cyanex 741X extractant has potential in the separation of palladium from
chloride solutions containing platinum(IV) and palladium(II). Palladium
extraction occurs with silver through a solvating mechanism. Stabilized
thiosulfate solutions are an effective strip feed. If present, Ag, Hg(II), Au(III)
will be co-extracted with palladium.

2.8 Scope of Solvent extraction with cyanex compounds

Extraction of metals by cyanex compounds takes place by ion-pair
extraction. In the present days large numbers of cyanex compounds are using
because of their selective extraction properties. In the presence of various
counter anions the extraction properties of cyanex compounds differs and
provides wide variability to extract different metals. Literature survey reveals
the applicability of cyanex compounds in separation of metals by solvent
extraction. The literature survey of cyanex compounds used in the extraction of
various metal ions is given in the following table 2.8.

22

Part I Chapter 2: Introduction to Cyanex

Table 2.8 Different cyanex compounds used for various metal extractions
under different conditions

Sr.

Cation

Technique

Cyanex

Media

Solvent

no.

Ref.
No.

Ga(III)

SE

CX-921

HCl

Toluene

Pd(II)

SE

CX-302

HCl

Toluene

Zn(II)

SE

CX-923

HCl

Solvesso-

100
4

Pd(II)

Ex-Chrom.

CX-302

0.1M HNO3

Au(III)

SE

CX-302

HCl

Zn(II)

SFC

CX-302

Am(III)

Ex-Chrom.

CX-301

HNO3

5
Toluene

CO2

Silica-

Polym.
8

Zn(II)

SE

CX-923

HCl

Ag(I)

BLM

CX-471X

HNO3

9
Alkenes +

10

Isodecanol
10

Co(II), Ni(II)

SLM

CX-

H2SO4

11

12

272,301,302
11

Cd(II)

Ex-Chrom.

CX-301

H3PO4

12

Am(III), Eu(III)

SE

CX-301

HNO3

Kerosene

13

13

Cr(III)

SE

CX-301

HCl

Toluene

14

14

As(III), (V)

SE

CX-925

H2SO4

Toluene

15

15

V(IV)

Ex-Chrom.

CX-272,

Silica Gel

16

17

CX-301
16

Ln(III)

HPCPC

CX-302

HCl

17

Ti(IV)

SE

CX-272

HCl

23

Xylene

18

Part I Chapter 2: Introduction to Cyanex

18

Sc(III)

SE

CX 923,

HCl

19

CX 925
19

Rh, Pt, Pd

SE

CX 921

HCl

Toluene

20

Os, Ru, Ir

SE

CX 921

HCl

21

21

Sc, Y, La, Gd

SE

CX 302

HCl

22

22

Ce, Th

SE

CX 923

H2SO4

23

Th(IV)

SE

CX 272

HNO3

24

U(VI)

SE

CX 272

Salicylate

Toluene

25

25

Th(IV)

SE

CX 272

Salicylate

Kerosene

26

26

Cu(II)

SE

CX 921

HCl

Kerosene

27

27

Be(II)

SE

CX 921

H2SO4

Kerosene

28

28

Ln(III), Y(III)

SE

CX 925

HNO3

n-heptane

29

29

Eu(III)

SE

CX 921

HNO3

Toluene

30

30

Al(III)

SE

CX 272

H2SO4

Exxsol D-80

31

31

Zr(IV), Hf(IV)

SE

CX 921,

HNO3

Kerosene

32

HCl

Toluene

33

n-hexane

20

23
24

923, 925
32

Pt(IV)

SE

CX 921,
925

33

La(III)

SE

CX 923

HNO3

Heptane

34

34

U(VI)

SE

CX 302

HNO3

Kerosene

35

35

Ln(III), Y(III)

SE

CX 925

HNO3

n-heptane

36

36

Ln(III), Sm(III)

SE

CX

HNO3

Kerosene

37

921,923,925
37

Cu(II)

SE

CX 272

24

H2SO4

38

Part I Chapter 2: Introduction to Cyanex

38

Co(II), Ni(II)

SE

CX 272

H2SO4

DX 3641

39

39

Zn, Ni

SE

CX 272,

H2SO4

Kerosene

40

D2EHPA
40

Ni(II)

SE

CX 272

H2SO4

Kerosene

41

41

Cd(II)

SE

D2EHPA

H2SO4

Toluene

42

42

Zr(IV)

SE

CX 272

HCl

Toluene

43

443

CO(II)

SE

CX 272

CH3COONa

Toluene

44

44

CU(II), Zn(II)

SE

CX 272,

H2SO4

Kerosene

45

HCl

Kerosene

46

H2SO4

Kerosene

47

Kerosene

48

Cyclohexane

49

Versatic 10
acid
45

Cd, Ni, Co

SE

Cx 272,
923, TOPS

46

Al, Ni

SE

TOPS 99,
PC 88 A,
CX 272

47

Ga(III), Al(III)

SE

DBTPA,
DETPA

48

Be(II), Al(III)

SE

CX 921

49

Cd, Co, Ni

SE

CX 923

HCl

Kerosene

50

50

Cd(II)

SLM

CX 923

HCl

Solvesso

51

100
51

Ti(IV)

SE

CX 923

HCl

Xylene

52

52

Mo(VI), W(VI)

SE

CX 923

HCl

Toluene

53

53

U(VI)

SE

CX 923

HNO3

Xylene

54

54

Rh, Pt, Pd

SE

CX 921

HCl

Toluene

55

55

Sc(III)

SE

CX 923,

H2SO4/ HCl

25

56

Part I Chapter 2: Introduction to Cyanex

925

57

Ln(III)

SE

CX 272

HClO4

57

58

Sn(II)

SE

CX 925

HCl

Toluene

58

59

Zn(II)

SE

CX 923

NH4Cl

Solvesso

59

100
60

U(VI), TH(IV)

SE

CX 923

HBr

Toluene

60

61

U(VI), Th(IV)

SE

CX 923

HNO3

Xylene

61

62

U(VI),Th(IV),Ce(III),

SE

CX 923

Mineral

Toluene

62

Ce(IV), Y(III)

acids

63

Th(IV)

SE

PC-88A

Chloride

Dodecane

63

64

Th(IV), Pr(III)

SE

CX 301,

Nitrate

Kerosene

64

Nitrate

Kerosene

65

Kerosene

66

302
65

Th(IV)

SE

CX 272

66

Ti(IV), V(V), Fe(III)

SE

CX 923

67

U(VI)

SE

CX 302

HNO3

Xylene

67

68

Sc(II), Zr(IV),

SE

CX 302,

Acidic

n-hexane

68

Th(IV), Fe(III),

301

Lu(III)
69

Mn(II)

SE

CX 302

Sulphate

Kerosene

69

70

Pb(II)

SE

CX 302

Phosphoric

Toluene

70

acid
71

Au(III)

SE

CX 471X

HCl

71

72

U(VI)

SE

CX 302,

HCl/ HNO3

Toluene

72

H2SO4

n-hexane

73

Alamine
308, TBP,
73

Ce(IV), Th(IV)

SE

CX 923

26

Part I Chapter 2: Introduction to Cyanex

74

Zr(IV)

SE

CX 923

Mineral

Toluene

74

acids
75

Ce(III), La(III)

SE

LIX 54

NaCl

n-heptane

75

76

Ti(IV)

SE

PC-88 A

HClO4

Toluene

76

In the present study we have concentrated on the separation of

lanthanides and actinides using cyanex compounds. The lanthanides and
actinides show very close properties. Since, in these elements, the number of
electrons in the outermost as well as the penultimate shell remains the same
and is very difficult to separate from one another [77]. In the present work we
have developed a reliable analytical method for extraction and separation of
uranium, thorium and cerium. Still there were no reports for extraction and
separation of uranium and thorium using cyanex 272 from sodium salicylate
medium in toluene and kerosene respectively. We have also carried out the
study of extraction and separation of cerium using cyanex 923 from sodium
acetate medium in kerosene. In the present work we have studied various
parameters like, concentration of cyanex extractant, concentration of counter
anion, effect of diluents, tolerance limit, multicomponent mixture separation.
The developed methods we have applied for the extraction and separation of
metal ions from real and geological samples.

27

Part I Chapter 2: Introduction to Cyanex

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