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Progress of Yara`s tasks
Hydromet project meeting
October 5, 2016
Alessio Vascon
Alexander Krivokapic
5 October 2016 Slide 2Hydromet project meeting
Outline
• The Odda process: challenges and possible solutions
• KELEX 100: continuation of studies
• APDC and elemental S: trials
• CYANEX 301: solvent extraction studies
• CYANEX 301: chemical stability studies
• CYANEX 301: stripping studies
• Possible future alternatives
• Summary
Slide 3Hydromet project meeting
The Odda process
DigestionCa5(PO4)3F (s) + 10HNO3 (aq) → 5Ca(NO3)2 (aq) + 3H3PO4 (aq) + HF (g)
Ca5(PO4)3F
(apatite)HNO3
Crystallization
Insolubles
Cooling Ca(NO3)2·4H2O
NeutralizationNH3 gas
Evaporation &
ParticulationPotassium
salt
NPK fertilizer products
5 October 2016
15 June 2016 Slide 4Hydromet project meeting
Presence of toxic contaminants: which ones to remove and from where?
Cd (<10 ppm)
DigestionCa5(PO4)3F
(apatite)HNO3
Crystallization
Insolubles
Cooling Ca(NO3)2·4H2O
NeutralizationNH3 gas
Evaporation &
ParticulationPotassium
salt
NPK fertilizer products
Crystallization Neutralization
pH ~ 0.5
(or pH ~ 1.8 with dilution 1/13)
Slide 5Hydromet project meeting
How to remove Cd?
Magnetic particles(particles with a magnetic core coated with a surface coating and
functional groups chosen for the specific application)
Functional groups
for Cd removal?
Solvent extraction
studies
5 October 2016
Slide 6Hydromet project meeting
KELEX 100 reference
0.3 M HNO3/H3PO4 _ 1h
0.3 M HNO3/H3PO4 _ 72h
3 M HNO3/H3PO4 _ 1h
3 M HNO3/H3PO4 _ 72h
KELEX 100
«nitro» KELEX 100
«nitro» KELEX 100
«nitro» KELEX 100
«nitro» KELEX 100
KELEX 100: previously…
KELEX 100 in acidic HNO3/H3PO4 environments:
5 October 2016
5 October 2016 Slide 7Hydromet project meeting
KELEX 100: previously…
KELEX 100 in acidic HNO3/H3PO4 environments:
N
OH
NO2
N+
OH
NO2
O-
chemically unstable
N
OH
5,0 5,5 6,0 6,5 7,0 7,5 8,0 8,5 9,0
0
10
20
30
40
50
60
70
80
90
100 Average of 3 parallels
Cd e
xtr
action (
%)
Equilibrium pH
0,0 0,5 1,0 1,5 2,0 2,5 3,00
1
2
3
4
5
Average of 3 parallels
Cd e
xtr
action (
%)
Equilibrium pH
(HNO3/H3PO4 solution)
(HNO3/H3PO4 solution)
0,5 1,0 1,5 2,0 2,5 3,00
1
2
3
4
5
Average of 3 parallels
Cd e
xtr
action (
%)
Equilibrium pH
(H3PO4 solution)
5 October 2016 Slide 8Hydromet project meeting
KELEX 100: previously…
Z. Marczenko, M. Balcerzak, Separation, Preconcentration and Spectrophotometry
in Inorganic Analysis (2000), 1st ed., Elsevier
Cd extraction with «nitro» KELEX 100
1000 rpm
Aqueous phase: 0.3 M HNO3/H3PO4 (pH theor. ~ 0.5)
Organic phase: KELEX 100 (0.02 M) in decane/1-decanol (10% vol)
Heating
90 °C / 6 h
centrifugation &
separation
5 October 2016 Slide 9Hydromet project meeting
N
OH
NO2
N+
OH
NO2
O-
N
OH+
5 October 2016 Slide 10Hydromet project meeting
Cd extraction with «nitro» KELEX 100
O: KELEX 100 (0.02 M)
in decane/1-decanol (10% vol)
A: H3PO4 sol. and HNO3/H3PO4 sol.
(10 ppm Cd) eq. pH 0.5-8.5
0 1 2 3 4 5 6 7 8 91E-3
0,01
0,1
1
10
100 "Nitro" KELEX 100 in H3PO4
"Nitro" KELEX 100 in HNO3 / H3PO4
Cd d
istr
ibution r
atio (
DC
d)
Equilibrium pH
0 1 2 3 4 5 6 7 8 9
0
20
40
60
80
100 "Nitro" KELEX 100 in H3PO4
"Nitro" KELEX 100 in HNO3 / H3PO4
Cd e
xtr
action (
%)
Equilibrium pH
O:A = 1:1
Cd extraction with «nitro» KELEX 100
5 October 2016 Slide 11Hydromet project meeting
ΔpH0.5 ~ 1.5
0 1 2 3 4 5 6 7 8 91E-3
0,01
0,1
1
10
100 "Nitro" KELEX 100 in H3PO4
"Nitro" KELEX 100 in HNO3 / H3PO4
KELEX 100
Cd
dis
trib
utio
n r
atio
(D
Cd)
Equilibrium pH
0 1 2 3 4 5 6 7 8 9
0
20
40
60
80
100 "Nitro" KELEX 100 in H3PO4
"Nitro" KELEX 100 in HNO3 / H3PO4
KELEX 100
Cd
extr
actio
n (
%)
Equilibrium pH
5 October 2016 Slide 12Hydromet project meeting
Cd extraction with «nitro» KELEX 100
N
OH
NO2
N+
OH
NO2
O-
N
OH
or
NO2 = strongly electron withdrawing group → more acidic KELEX 100 (pKa ↓)
5-chloro-8-quinolinol 5,7-dichloro-8-quinolinol
chemical instability can be helpful !!
Cd extraction with APDC: previously…
5 October 2016 Slide 13Hydromet project meeting
Ammonium pyrrolidine dithiocarbamate
(APDC)
+Methyl
isobutyl ketone
(MIBK)
Organic phase Aqueous phase
HNO3 sol.
(0-6 M)
R. Brooks et al., Analytica Chimica Acta 217 (1989) 165-170
5 October 2016 Slide 14Hydromet project meeting
Cd extraction with APDC: trials
O: methyl isobutyl ketone
(MIBK)
A: HNO3/H3PO4 sol., 0.02 M APDC
(10 ppm Cd) eq. pH 0.5-8.5
APDC in 0.3 M HNO3 / H3PO4APDC APDC in H2O(to be stored at + 4°C)
O:A = 1:1
Variations in Extraction Efficiency of Aqueous Cadmium (II) Using the APDC-MIBK Procedure, L.W. Newland, R.G. Clements.
Cd extraction with APDC: trials
Slide 15Hydromet project meeting5 October 2016
APDC 99% (Sigma-Aldrich) → 25 g ~ 3000 NOK
Cd extraction with elemental S: trials
Cd-rich
cake
Cd-free
filtrate
0.3 M HNO3 / H3PO4
10 ppm Cd + 109Cd tracer
Slide 16Hydromet project meeting5 October 2016
0 100 200 300 400 500 600
0
500
1000
1500
2000
Counts
Channel
Before S8 test (starting sol.)
After S8 test (filtrate)
Cd extraction with CYANEX 301
Slide 17Hydromet project meeting5 October 2016
+Kerosene
(ASOL D80)
Organic phase Aqueous phase
HNO3/H3PO4 sol.
(pH 0.5-2)
Cyanex 301
di-(2,4,4-trimethyl pentyl)phosphinic acid
K.C. Sole et al., Solvent Extraction and Ion Exchange 11 (1993) 783-796
P. Marc et al., Industrial & engineering chemistry research 51 (2012) 13238-13244
+ Stripping (?)
CYANEX 301: solvent extraction studies
Slide 18Hydromet project meeting5 October 2016
Equilibrium kinetics study
O: CYANEX 301 (0.02 M)
in ASOL D80
A: HNO3/H3PO4 sol.
eq. pH 1.7±0.1
10 20 30 40 50 600
20
40
60
80
100
Average of 3 parallels
Cd e
xtr
action (
%)
Shaking time (min)
O:A = 1:1
CYANEX 301: solvent extraction studies
Slide 19Hydromet project meeting5 October 2016
O: CYANEX 301 (0.02 M)
in ASOL D80
A: HNO3/H3PO4 sol.
eq. pH 0-5
0 1 2 3 4 50,1
1
10
100
1000
Average of 3 parallels
Cd
dis
trib
utio
n r
atio
(D
Cd)
Equilibrium pH
0 1 2 3 4 50
20
40
60
80
100 Average of 3 parallels
Cd
extr
actio
n (
%)
Equilibrium pH
O:A = 1:1
pH 0-1.5 O:A = 1:1; n = 1 → DCd ~ 135 / Ecd ~ 99.3%
Slide 20Hydromet project meeting5 October 2016
CYANEX 301: solvent extraction studies
1,5 2,0 2,5 3,0 3,5 4,0 4,5 5,00,1
1
10
100
1000
Average of 3 parallels
Linear fitting
Cd
dis
trib
utio
n r
atio
(D
Cd)
Equilibrium pH
Equation y = a + b*x
Weight Instrumental
Residual Sum of Squares
179,75456
Pearson's r -0,9899
Adj. R-Square 0,95982
Value Standard Error
D ratioIntercept 3,70201 0,42203
Slope -0,99651 0,14269
CYANEX 301: chemical stability studies
Slide 21Hydromet project meeting5 October 2016
1000 rpm
Aqueous phase: 0.3 M HNO3/H3PO4 (pH theor. ~ 0.5)
Organic phase: CYANEX 301 (0.02 M) in ASOL D80
3 M HNO3/H3PO4 (pH theor. ~ -5)
Heating
90 °C / 7 h
centrifugation &
separation
0,0 0,2 0,4 0,6 0,8 1,0 1,2 1,4 1,61E-3
0,01
0,1
1
10
100
1000
"Nitro" CYANEX 301 (0.3M / 7h)
CYANEX 301
"Nitro" CYANEX 301 (3M / 7h)
Cd d
istr
ibution r
atio (
DC
d)
Equilibrium pH
0,0 0,2 0,4 0,6 0,8 1,0 1,2 1,4 1,6
0
20
40
60
80
100
"Nitro" CYANEX 301 (0.3M / 7h)
CYANEX 301
"Nitro" CYANEX 301 (3M / 7h)
Cd e
xtr
action (
%)
Equilibrium pH
CYANEX 301: chemical stability studies
Slide 22Hydromet project meeting5 October 2016
1000 rpm
Aqueous phase: 0.3 M HNO3/H3PO4 (pH theor. ~ 0.5)
Organic phase: CYANEX 301 (0.02 M) in ASOL D80
Heating
90 °C / 24 h
centrifugation &
separation
0,0 0,2 0,4 0,6 0,8 1,0 1,2 1,4 1,6 1,8 2,01E-3
0,01
0,1
1
10
100
1000
"Nitro" CYANEX 301 (0.3M / 24h)
CYANEX 301
Cd d
istr
ibution r
atio (
DC
d)
Equilibirum pH
0,0 0,2 0,4 0,6 0,8 1,0 1,2 1,4 1,6 1,8 2,0
0
20
40
60
80
100
"Nitro" CYANEX 301 (0.3M / 24h)
CYANEX 301
Cd e
xtr
action (
%)
Equilibirum pH
CYANEX 301: stripping studies
Slide 23Hydromet project meeting5 October 2016
B. Ramachandra Reddy et al., Separation and Purification Technology 50 (2006) 161-166
CYANEX 301: stripping studies
Slide 24Hydromet project meeting5 October 2016
0 20 40 60 80 100 1201E-3
0,01
0,1
1
Average of 3 parallels
Cd d
istr
ibution r
atio (
DC
d)
Shaking time (min)
0 20 40 60 80 100 1200
20
40
60
80
100
Average of 3 parallelsC
d s
trip
pin
g (
%)
Shaking time (min)
O: CYANEX 301 (0.02 M)
in ASOL D80
A: HCl (6 M)O:A = 1:1
Fast kinetics O:A = 1:1; n = 1 → DCd ~ 8·10-3 / Ecd(aq) ~ 99.2%
Possible alternatives…
Slide 25Hydromet project meeting5 October 2016
+ 1,2-dichloroethane
Organic phase Aqueous phase
HNO3 sol.
(0-7 M)
(diphenylphosphinylmethyl)phenylphosphinic acids -HA-
Possible alternatives…
Slide 26Hydromet project meeting5 October 2016
Log D ~ 0.5 → E ~ 75%
Log D ~ 0.75 → E ~ 85%
Log D ~ -0.4 → E ~ 30%
Log -0.5 M = 0.3 M
Summary
• KELEX 100 studies → chemical instability of the molecule can be helpful
• APDC and elemental S studies → unsuccessful
• CYANEX 301 → ECd > 99% @ pH 0.5 with O:A = 1:1
• CYANEX 301 → precarious chemical stability in HNO3/H3PO4 environments
• CYANEX 301 → Ecd(aq) > 99% with HCl 6 M and O:A = 1:1
• (diphenylphosphinylmethyl)phenylphosphinic acids → a possible future
alternative for Cd removal and REEs extraction ?
Slide 28Hydromet project meeting5 October 2016
Discussion points...
Slide 30Hydromet project meeting5 October 2016
• Are the chemical stability studies representative of the industrial conditions?
• Can CYANEX 301 considered to be ok for the development of the studies?
• Are lower HCl concentrations to be sought for stripping of CYANEX 301?
• What about (diphenylphosphinylmethyl)phenylphosphinic acids? Could they
be of any interest?
Slide 31Hydromet project meeting
KELEX 100: solvent extraction studies
+KELEX 100 (0.02 M)
in decane/1-decanol (10% vol)
HNO3/H3PO4 or H3PO4 solutions
(containing 10 ppm Cd)
at different pH values
109Cd in
0.05 M HNO3 =O/A: 1/1
shaking
(according to proper
equilibrium kinetics study)centrifugation
aqueous
organic
liquid scintillation counting
(after proper efficiency calibration)
0 100 200 300 400 500
0
200
400
600
800
1000
Counts
Channel
5 October 2016
Slide 32Hydromet project meeting
KELEX 100: solvent extraction studies
pH measurement
-50 0 50 100 150 200 250 300 350
1
2
3
4
5
6
7
pH
Voltage (mV)
Equation y = a + b*x
Weight No Weighting
Residual Sum of Squares
0,013
Pearson's r -0,99964
Adj. R-Square 0,99856
Value Standard Error
pHIntercept 6,5068 0,09413
Slope -0,01763 4,73902E-4
-150 -100 -50 0 50 100 150 200
4
5
6
7
8
9
pH
Voltage (mV)
Equation y = a + b*x
Weight No Weighting
Residual Sum of Squares
0,01954
Pearson's r -0,99923
Adj. R-Square 0,9969
Value Standard Error
pHIntercept 6,62549 0,08073
Slope -0,01734 6,83113E-4
5 October 2016
Slide 33Hydromet project meeting
KELEX 100 chemical stability studies: LC-ESI-MS results
C:\Xcalibur\...\Alex\Alex-Relex-t=0 06/01/16 14:09:30
RT: 0.00 - 30.01 SM: 7B
0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30
Time (min)
0
50
100
0
50
100
0
50
100
Re
lative
Ab
un
da
nce
0
50
1007.97
1.82 7.32 19.937.13 23.528.27 22.97 23.7310.11 14.6610.39 18.77 21.5413.3812.09 15.18 18.56 24.83 25.97 27.551.61 28.413.39 3.85 6.305.31
15.39
22.9722.55 23.1024.1817.80
25.41 26.4317.1213.80 18.56 27.49 28.4919.179.95
15.96
1.77 11.327.876.66
7.67 9.749.94 16.86
14.8827.35
29.446.61
NL: 1.17E10
TIC F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-t=0
NL: 1.16E7
m/z= 300.22719-300.23719 F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-t=0
NL: 2.96E4
m/z= 345.21226-345.22226 F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-t=0
NL: 1.36E4
m/z= 361.20718-361.21718 F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-t=0
Alex-Relex-t=0 #2629 RT: 15.38 AV: 1 NL: 1.07E7T: FTMS + p ESI Full ms [100.00-1000.00]
299.2 299.4 299.6 299.8 300.0 300.2 300.4 300.6 300.8 301.0 301.2 301.4
m/z
0
10
20
30
40
50
60
70
80
90
100
Re
lative
Ab
un
da
nce
300.23074
C 20 H30 O N
301.23410
299.30420299.21872300.28830
C 18 H38 O 2 N 300.91885299.91125
Reference organic phase: KELEX 100 (0.02 M) in decane/1-decanol (10% vol)
N
OH
Molecular Formula = C20H29NO
Formula Weight = 299.45036
5 October 2016
Slide 34Hydromet project meeting
KELEX 100 chemical stability studies: LC-ESI-MS results
Organic phase after reaction with 0.3 M HNO3/H3PO4 solution for 1h at 90 °C
C:\Xcalibur\...\Alex-Relex-0_3M-1hour 06/01/16 14:51:29
RT: 0.00 - 30.01 SM: 7B
0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30
Time (min)
0
50
100
0
50
100
0
50
100
Re
lative
Ab
un
da
nce
0
50
1008.08
17.31 17.4617.20 19.917.411.81 20.037.12 18.10 23.3323.0014.55 23.7814.1112.778.54 14.9711.55 24.769.49 26.431.62 27.25 28.532.37 3.40 5.794.30
17.31
17.62
17.84
18.63 19.21 20.56 22.05 22.87 23.61 25.1516.32 26.33 27.4115.57 28.4714.3913.5112.3711.3310.29
20.69
17.48
16.131.61 14.8213.11 27.52
16.88
20.641.80
20.721.75 16.959.84 26.7716.77 27.42
NL: 9.33E9
TIC F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-0_3M-1hour
NL: 3.24E9
m/z= 300.22719-300.23719 F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-0_3M-1hour
NL: 1.76E6
m/z= 345.21226-345.22226 F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-0_3M-1hour
NL: 3.45E4
m/z= 361.20718-361.21718 F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-0_3M-1hour
Alex-Relex-0_3M-1hour #3636 RT: 20.68 AV: 1 NL: 1.50E6T: FTMS + p ESI Full ms [100.00-1000.00]
342 343 344 345 346 347 348 349 350 351 352
m/z
0
10
20
30
40
50
60
70
80
90
100
Re
lative
Ab
un
da
nce
345.21567
C 20 H29 O 3 N2
346.21890
C 24 H28 O N
344.22650
C 24 H28 N2 350.33612
N
OH
NO2
Molecular Formula = C20H28N2O3
Formula Weight = 344.44792
5 October 2016
Slide 35Hydromet project meeting
KELEX 100 chemical stability studies: LC-ESI-MS results
Organic phase after reaction with 0.3 M HNO3/H3PO4 solution for 72h at 90 °C
C:\Xcalibur\...\Alex-Relex-0_3M-72hours 06/01/16 15:33:20
RT: 0.00 - 30.01 SM: 7B
0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30
Time (min)
0
50
100
0
50
100
0
50
100
Re
lative
Ab
un
da
nce
0
50
1008.06
16.19 17.28
18.527.291.82 15.627.02 19.458.47 23.3212.74 13.3711.92 23.8820.37 23.168.99 24.632.04 26.80 27.421.64 28.662.62 4.75
17.1217.38
17.5017.0418.5216.21
18.76 20.9815.94 21.2715.23 22.86 23.8114.20 24.8612.62 25.97 27.0511.62 28.1710.549.331.63 8.585.094.50 5.62
15.54
16.08 16.86
18.2918.4315.40
13.75
16.20
15.52 18.9718.6514.959.83
NL: 8.76E9
TIC F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-0_3M-72hours
NL: 3.05E9
m/z= 300.23069-300.23369 F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-0_3M-72hours
NL: 1.53E5
m/z= 345.21553-345.21899 F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-0_3M-72hours
NL: 8.84E5
m/z= 361.21037-361.21399 F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-0_3M-72hours
Alex-Relex-0_3M-72hours #2780 RT: 16.23 AV: 1 NL: 9.03E5T: FTMS + p ESI Full ms [100.00-1000.00]
359.5 360.0 360.5 361.0 361.5 362.0 362.5 363.0 363.5 364.0 364.5 365.0
m/z
0
10
20
30
40
50
60
70
80
90
100
Re
lative
Ab
un
da
nce
362.26807
C 25 H34 N2
361.21088
C 20 H29 O 4 N2
360.19839
N+
OH
NO2
O-
Molecular Formula = C20H28N2O4
Formula Weight = 360.44732
5 October 2016
Slide 36Hydromet project meeting
KELEX 100 chemical stability studies: LC-ESI-MS results
Organic phase after reaction with 3 M HNO3/H3PO4 solution for 1h at 90 °C
C:\Xcalibur\...\Alex\Alex-Relex-3M-1hour 06/01/16 16:15:12
RT: 0.00 - 30.01 SM: 7B
0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30
Time (min)
0
50
100
0
50
100
0
50
100
Re
lative
Ab
un
da
nce
0
50
1008.07
7.297.181.81 17.268.34 19.45 23.0122.89 23.3611.37 17.14 19.248.84 24.51 26.02 26.9715.8011.83 20.49 28.0513.42 29.132.12 2.66 4.61 5.24
17.2716.20
16.0415.67 17.50
19.4414.62 20.52 22.1014.21 22.4213.19 23.5011.68 24.91 25.9510.35 27.119.27 28.148.611.72 3.95 5.013.26 6.10 6.51
18.26
22.4421.2021.08 23.36 23.7618.94 20.31
24.4317.53 25.1217.02
17.58
17.47
17.04 18.919.74 16.12
NL: 7.87E9
TIC F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-3M-1hour
NL: 4.03E8
m/z= 300.23069-300.23369 F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-3M-1hour
NL: 2.14E5
m/z= 345.21553-345.21899 F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-3M-1hour
NL: 6.34E4
m/z= 361.21037-361.21399 F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-3M-1hour
Alex-Relex-3M-1hour #1 RT: 1.57 AV: 1 NL: 3.39E7T: FTMS + p ESI Full ms [100.00-1000.00]
200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000
m/z
0
10
20
30
40
50
60
70
80
90
100
Re
lative
Ab
un
da
nce
201.11108
C 8 H15 O 3 N3
218.13757
C 8 H18 O 3 N4
391.28217
C 20 H35 O 2 N6257.24606
C 14 H31 O N3
593.15448
C 17 H25 O 14 N10
667.17218
C 26 H35 O 20
445.11743
C 12 H17 O 9 N10
519.13611
C 8 H25 O 17 N9
743.19049
C 30 H31 O 15 N8 867.20728 930.35315809.56683
5 October 2016
Slide 37Hydromet project meeting
KELEX 100 chemical stability studies: LC-ESI-MS results
Organic phase after reaction with 3 M HNO3/H3PO4 solution for 72h at 90 °C
C:\Xcalibur\...\Alex-Relex-3M-72hours 06/01/16 16:57:01
RT: 0.00 - 30.01 SM: 7B
0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30
Time (min)
0
50
100
0
50
100
0
50
100
Re
lative
Ab
un
da
nce
0
50
1008.09
1.79 7.337.20 18.15 18.2517.94 19.858.44 12.83 14.4412.0011.23 16.18 23.759.68 24.5123.54 28.2325.05 28.7820.80 26.112.22 3.12 4.84 5.801.67
16.15 16.29
17.27
15.96 17.6015.28 20.7318.22 20.8514.27 22.3513.16 23.1311.87 24.52 25.7410.50 26.71 28.119.40 29.304.82
16.26 16.4515.97
20.17 22.4215.80 17.62 22.5621.7815.39
14.74 23.9324.4713.96 25.58
20.31
20.21 20.5518.97
21.2716.81 21.4416.287.03 18.6113.47 23.90
NL: 6.80E9
TIC F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-3M-72hours
NL: 5.44E7
m/z= 300.23069-300.23369 F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-3M-72hours
NL: 3.41E5
m/z= 345.21553-345.21899 F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-3M-72hours
NL: 1.80E5
m/z= 361.21037-361.21399 F: FTMS + p ESI Full ms [100.00-1000.00] MS Alex-Relex-3M-72hours
Alex-Relex-3M-72hours #3292 RT: 19.00 AV: 1 NL: 1.01E5T: FTMS + p ESI Full ms [100.00-1000.00]
360.5 361.0 361.5 362.0 362.5 363.0 363.5 364.0 364.5 365.0
m/z
0
10
20
30
40
50
60
70
80
90
100
Re
lative
Ab
un
da
nce
361.21063
C 20 H29 O 4 N2
363.30881
362.19452
364.34149
C 23 H44 O N2
360.30951
N+
OH
NO2
O-
Molecular Formula = C20H28N2O4
Formula Weight = 360.44732
5 October 2016
Slide 38Hydromet project meeting
New bibliographic results: KELEX 100
KELEX 100
7-(4-ethyl-1-methyloctyl)-8-hydroxyquinoline
+kerosene
with (10% vol)
n-decanol
Organic phase Aqueous phase
H3PO4 sol.
(pH 0.5-4)
A. Mellah et al., Hydrometallurgy 81 (2006) 100-103
5 October 2016