Determination of Phthalate Esters in Beverages and Water Samples by Solid Phase Extraction with Resin Based COFs as Filler
Abstract
:1. Introduction
2. Materials and Methods
2.1. Reagents and Instruments
2.2. Experimental Methods
2.2.1. Preparation of COF Materials
2.2.2. Determination of PAEs Adsorption Behavior
2.2.3. SPE Experiment
2.2.4. Stability Experiment of Four PAEs
2.2.5. Precision Analysis of Four PAEs
2.2.6. Recovery of Four PAEs
2.2.7. Repetitive Experiment of Four PAEs
3. Results
3.1. Adsorption Behavior of Materials
3.1.1. Analysis of Adsorption Effect of COFS on PAEs
3.1.2. Static Adsorption Behavior of PAEs by COFs
3.1.3. Kinetic Adsorption Behavior of PAEs by COFs
3.2. Evaluation of SPE Performance
3.2.1. Analysis of Detection Conditions of PAEs by HPLC
3.2.2. Determination of Standard Curve of PAEs
3.2.3. Evaluation of the Effect of PAEs SPE Materials
3.2.4. Analysis of SPE Scheme for PAEs
3.2.5. Stability Analysis of Four PAEs
3.2.6. Precision Analysis of Four PAEs
3.2.7. Analysis of SPE Results of PAEs
3.2.8. Evaluation of Reuse Effect of Two COFs by SPE
4. Conclusions
- (1)
- Adsorption experiments showed that the kinetic adsorption behavior of COF materials for PAEs was more consistent with the quasi-second-order kinetic adsorption model, and the static adsorption behavior is more in line with the Freundlich isothermal adsorption model.
- (2)
- Two COF materials were applied to the SPE of PAEs samples. The recoveries were 97.99–100.56% and 97.93–100.23%, respectively. The most suitable solid phase extraction schemes are X-A and X-C. These two COFs had ideal enrichment and separation effect on four phthalate esters, and had strong anti-interference ability. The SPE effects were better than four commercially available SPE columns.
- (3)
- The preparation cost of COF materials was greatly reduced after COF materials are compounded with resin. This study provided a new way to introduce COF materials as high performance SPE adsorbent for the preconcentration and determination of trace harmful substances in beverage samples.
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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c (mg L−1) | tRDMP (min) | tRDEP (min) | tRDBP (min) | tRDOP (min) | |
---|---|---|---|---|---|
TpBD COFs | 237.8 | 9.205 | 9.751 | 9.485 | 9.648 |
475.6 | 8.951 | 9.482 | 9.113 | 9.156 | |
713.4 | 8.769 | 9.189 | 8.947 | 9.012 | |
951.5 | 8.603 | 8.859 | 8.558 | 8.809 | |
1189 | 8.595 | 8.734 | 8.325 | 8.415 | |
Resin based COFs | 237.8 | 8.925 | 9.485 | 9.225 | 9.501 |
475.6 | 8.751 | 9.113 | 8.999 | 9.098 | |
713.4 | 8.595 | 8.951 | 8.702 | 8.901 | |
951.5 | 8.485 | 8.603 | 8.452 | 8.691 | |
1189 | 8.382 | 8.558 | 8.21 | 8.348 |
Material | Analyte | ||||||||
---|---|---|---|---|---|---|---|---|---|
Linear Formula | R2 | qm (mg·g−1) | KL (×10−5) | Linear Formula | R2 | n | KF | ||
TpBD COFs | DMP | y = 0.000838x + 10.741 | 0.909 | 1193.32 | 7.802 | y = 0.954x − 0.928 | 0.999 | 1.048 | 0.118 |
DEP | y = 0.00141x + 9.945 | 0.983 | 709.22 | 1.417 | y = 0.929x − 0.841 | 0.999 | 1.076 | 0.144 | |
DBP | y = 0.00175x + 10.183 | 0.984 | 571.43 | 1.178 | y = 0.921x − 0.837 | 0.999 | 1.085 | 0.145 | |
DOP | y = 0.00176x + 10.083 | 0.952 | 568.18 | 1.745 | y = 0.923x − 0.837 | 0.999 | 1.083 | 0.145 | |
Resin based COFs | DMP | y = 0.000761x + 11.053 | 0.986 | 1314.06 | 6.885 | y = 0.961x − 0.955 | 0.999 | 1.045 | 0.111 |
DEP | y = 0.00132x + 10.319 | 0.944 | 757.58 | 1.279 | y = 0.934x − 0.867 | 0.999 | 1.071 | 0.136 | |
DBP | y = 0.00163x + 10.471 | 0.997 | 613.50 | 1.556 | y = 0.928x − 0.864 | 0.999 | 1.077 | 0.136 | |
DOP | y = 0.00174x + 10.219 | 0.979 | 574.71 | 1.702 | y = 0.925x − 0.848 | 0.999 | 1.081 | 0.141 |
Material | Analyte | ||||||
---|---|---|---|---|---|---|---|
Linear Formula | R2 | K1/(1 min−1) | Linear Formula | R2 | K2 (10−3·g/(mg·min)) | ||
TpBD COFs | DMP | y = −0.315x + 5.506 | 0.696 | 0.315 | y = 0.0272x − 0.157 | 0.963 | 0.027 |
DEP | y = −0.253x + 5.169 | 0.790 | 0.253 | y = 0.0169x − 0.0886 | 0.975 | 0.0170 | |
DBP | y = −0.275x + 5.129 | 0.754 | 0.275 | y = 0.0219x − 0.113 | 0.964 | 0.022 | |
DOP | y = −0.247x + 4.901 | 0.775 | 0.247 | y = 0.0184x − 0.0855 | 0.981 | 0.018 | |
Resin based COFs | DMP | y = −0.300x + 5.357 | 0.718 | 0.300 | y = 0.0239x − 0.129 | 0.980 | 0.024 |
DEP | y = −0.259x + 5.103 | 0.782 | 0.259 | y = 0.0179x − 0.0882 | 0.968 | 0.018 | |
DBP | y = −0.275x + 5.101 | 0.754 | 0.275 | y = 0.0220x − 0.111 | 0.971 | 0.022 | |
DOP | y = −0.262x + 4.959 | 0.749 | 0.262 | y = 0.0211x − 0.102 | 0.987 | 0.021 |
PAEs | Linear Equation | R2 | LOD (μg/L) | RSD (%) n = 5 |
DMP | y = 8.64 × 107 × x − 7.14 × 104 | 0.997 | 0.02 | 0.118 |
DEP | y = 8.39 × 107 × x + 8.65 × 103 | 0.992 | 0.05 | 0.149 |
DBP | y = 8.26 × 107 × x + 3.84 × 105 | 0.996 | 0.01 | 0.127 |
DOP | y = 2.13 × 108 × x + 2.75 × 105 | 0.991 | 0.06 | 0.306 |
Sorbent | Method | Sample | Elution Solution | Recovery | Ref |
---|---|---|---|---|---|
GO@LDH@SPAN | GC-MS | water and beverage | methanol | 54.5–112.6% | [28] |
Nanofiber pad | SPE-HPLC | tap water, rainwater and pool water | acetonitrile, methanol | >88% | [29] |
polysulfone hollow fiber | SPME-FE/GC | water | ethanol | 87.0–117.7% | [30] |
CuFe2O4 Nanoparticles | SPME | water | water | 81.1–103.7% | [31] |
Graphene modified COF | HS-SPME-GC-MS | water | 10% (w/v) salt | 80.5–111.0% | [32] |
TpBD COFs | SPE-HPLC | water and beverage | methanol | 98.26–100.56% | This work |
Resin based COFs | 97.99–99.30% |
Sample | Method | Material | Recovery (%, n = 3) | Material | Recovery (%, n = 3) | Material | Recovery (%, n = 3) |
---|---|---|---|---|---|---|---|
DMP | X | Market | 89.69 | TpBD COFs | 93.51 | Resin based COFs | 70.23 |
X-CW | 70.62 | 99.23 | 62.46 | ||||
X-A | 80.56 | 90.38 | 99.21 | ||||
X-C | 62.31 | 90.56 | 99.99 | ||||
DEP | X | 86.71 | 92.87 | 69.13 | |||
X-CW | 68.75 | 99.99 | 60.35 | ||||
X-A | 82.56 | 92.51 | 99.23 | ||||
X-C | 68.89 | 91.88 | 99.87 | ||||
DBP | X | 85.99 | 94.62 | 75.78 | |||
X-CW | 60.23 | 97.80 | 59.12 | ||||
X-A | 86.89 | 92.61 | 96.56 | ||||
X-C | 65.26 | 91.10 | 95.30 | ||||
DOP | X | 59.56 | 90.83 | 80.89 | |||
X-CW | 30.25 | 78.92 | 98.73 | ||||
X-A | 83.45 | 98.99 | 96.18 | ||||
X-C | 30.23 | 98.00 | 92.89 |
Analyte | Method | Peak Area (×106) | Average (×106) | SD (×106) | RSD (%) | |||||
---|---|---|---|---|---|---|---|---|---|---|
Mixture1 | X-A | DMP | 2.18 | 2.17 | 2.15 | 2.16 | 2.16 | 2.164 | 0.0114 | 0.526 |
DEP | 2.16 | 2.16 | 2.16 | 2.14 | 2.15 | 2.154 | 0.00894 | 0.415 | ||
DBP | 1.47 | 1.46 | 1.49 | 1.46 | 1.46 | 1.468 | 0.0130 | 0.888 | ||
DOP | 1.39 | 1.40 | 1.38 | 1.39 | 1.40 | 1.392 | 0.00836 | 0.601 | ||
X-C | DMP | 2.34 | 2.36 | 2.32 | 2.34 | 2.35 | 2.342 | 0.0148 | 0.633 | |
DEP | 2.18 | 2.18 | 2.18 | 2.17 | 2.17 | 2.176 | 0.00547 | 0.251 | ||
DBP | 1.48 | 1.47 | 1.5 | 1.47 | 1.46 | 1.476 | 0.0151 | 1.027 | ||
DOP | 1.42 | 1.42 | 1.42 | 1.40 | 1.40 | 1.412 | 0.0109 | 0.775 | ||
Mixture2 | X-A | DMP | 3.99 | 3.99 | 4.02 | 4.00 | 3.98 | 3.996 | 0.0151 | 0.379 |
DEP | 3.32 | 3.32 | 3.34 | 3.33 | 3.32 | 3.326 | 0.00894 | 0.268 | ||
DBP | 2.61 | 2.60 | 2.60 | 2.60 | 2.60 | 2.602 | 0.00447 | 0.171 | ||
DOP | 1.92 | 1.90 | 1.93 | 1.91 | 1.90 | 1.912 | 0.0130 | 0.681 | ||
X-C | DMP | 4.85 | 4.83 | 4.86 | 4.82 | 4.82 | 4.836 | 0.0181 | 0.375 | |
DEP | 2.92 | 2.92 | 2.90 | 2.90 | 2.91 | 2.910 | 0.010 | 0.343 | ||
DBP | 2.88 | 2.9 | 2.87 | 2.89 | 2.87 | 2.882 | 0.0130 | 0.452 | ||
DOP | 2.23 | 2.23 | 2.21 | 2.22 | 2.23 | 2.224 | 0.00894 | 0.402 |
Analyte | Method | Peak Area (×106) | Average (×106) | SD (×106) | RSD (%) | |||||
---|---|---|---|---|---|---|---|---|---|---|
Mixture1 | X-A | DMP | 2.28 | 2.26 | 2.31 | 2.30 | 2.34 | 2.298 | 0.0303 | 1.31 |
DEP | 2.17 | 2.18 | 2.18 | 2.20 | 2.19 | 2.184 | 0.0114 | 0.52 | ||
DBP | 1.49 | 1.42 | 1.58 | 1.56 | 1.46 | 1.502 | 0.0672 | 2.47 | ||
DOP | 1.42 | 1.44 | 1.48 | 1.39 | 1.50 | 1.446 | 0.0444 | 3.07 | ||
X-C | DMP | 2.74 | 2.68 | 2.68 | 2.71 | 2.80 | 2.722 | 0.0502 | 1.84 | |
DEP | 2.30 | 2.31 | 2.32 | 2.32 | 2.32 | 2.314 | 0.0089 | 0.38 | ||
DBP | 1.56 | 1.67 | 1.63 | 1.51 | 1.70 | 1.614 | 0.0610 | 3.78 | ||
DOP | 1.70 | 1.72 | 1.82 | 1.86 | 1.86 | 1.792 | 0.0769 | 4.29 | ||
Mixture2 | X-A | DMP | 4.01 | 4.20 | 4.11 | 4.06 | 4.04 | 4.084 | 0.0743 | 1.82 |
DEP | 3.44 | 3.47 | 3.42 | 3.46 | 3.40 | 3.438 | 0.0286 | 0.83 | ||
DBP | 2.63 | 2.65 | 2.64 | 2.60 | 2.67 | 2.638 | 0.0258 | 0.98 | ||
DOP | 2.19 | 2.10 | 2.14 | 2.16 | 2.09 | 2.136 | 0.0415 | 1.94 | ||
X-C | DMP | 4.96 | 4.80 | 4.98 | 4.91 | 4.89 | 4.908 | 0.0704 | 1.43 | |
DEP | 3.04 | 3.22 | 3.08 | 3.13 | 3.16 | 3.126 | 0.0698 | 2.23 | ||
DBP | 2.91 | 2.90 | 2.68 | 2.81 | 2.87 | 2.834 | 0.0944 | 3.33 | ||
DOP | 2.25 | 2.14 | 2.51 | 2.25 | 2.16 | 2.262 | 0.0975 | 3.52 |
Sample | Method | Material | Targets | Spiked (μg/L) | Recovery (%, n = 3) |
---|---|---|---|---|---|
Water | X-C method | TpBD COFs | DMP | 10 | 98.99 |
20 | 100.56 | ||||
30 | 99.00 | ||||
40 | 98.75 | ||||
DEP | 10 | 99.11 | |||
20 | 99.23 | ||||
30 | 100.11 | ||||
40 | 100.35 | ||||
DBP | 10 | 99.99 | |||
20 | 99.45 | ||||
30 | 99.68 | ||||
40 | 99.87 | ||||
DOP | 10 | 99.91 | |||
20 | 98.99 | ||||
30 | 99.16 | ||||
40 | 99.99 | ||||
Resin based COFs | DMP | 10 | 98.26 | ||
20 | 98.56 | ||||
30 | 98.42 | ||||
40 | 98.80 | ||||
DEP | 10 | 97.99 | |||
20 | 98.27 | ||||
30 | 98.46 | ||||
40 | 99.30 | ||||
DBP | 10 | 98.97 | |||
20 | 98.71 | ||||
30 | 98.65 | ||||
40 | 98.72 | ||||
DOP | 10 | 98.61 | |||
20 | 98.75 | ||||
30 | 99.13 | ||||
40 | 98.79 | ||||
X-A method | TpBD COFs | DMP | 10 | 98.72 | |
20 | 98.90 | ||||
30 | 98.99 | ||||
40 | 98.60 | ||||
DEP | 10 | 99.10 | |||
20 | 98.99 | ||||
30 | 98.10 | ||||
40 | 98.76 | ||||
DBP | 10 | 98.88 | |||
20 | 98.60 | ||||
30 | 98.74 | ||||
40 | 98.56 | ||||
DOP | 10 | 99.16 | |||
20 | 99.26 | ||||
30 | 99.34 | ||||
40 | 98.91 | ||||
Resin based COFs | DMP | 10 | 98.85 | ||
20 | 98.66 | ||||
30 | 98.99 | ||||
40 | 98.39 | ||||
DEP | 10 | 98.79 | |||
20 | 98.83 | ||||
30 | 98.86 | ||||
40 | 99.15 | ||||
DBP | 10 | 98.10 | |||
20 | 98.44 | ||||
30 | 98.96 | ||||
40 | 98.08 | ||||
DOP | 10 | 99.11 | |||
20 | 99.01 | ||||
30 | 98.88 | ||||
40 | 98.56 | ||||
Vitamin beverage | X-C method | TpBD COFs | DMP | 10 | 99.23 |
20 | 99.56 | ||||
30 | 99.78 | ||||
40 | 99.91 | ||||
DEP | 10 | 100.01 | |||
20 | 99.88 | ||||
30 | 100.23 | ||||
40 | 100.15 | ||||
DBP | 10 | 99.46 | |||
20 | 99.87 | ||||
30 | 99.85 | ||||
40 | 99.45 | ||||
DOP | 10 | 99.61 | |||
20 | 99.99 | ||||
30 | 100.01 | ||||
40 | 99.00 | ||||
Resin based COFs | DMP | 10 | 98.80 | ||
20 | 98.86 | ||||
30 | 99.15 | ||||
40 | 98.85 | ||||
DEP | 10 | 98.79 | |||
20 | 98.88 | ||||
30 | 98.62 | ||||
40 | 98.56 | ||||
DBP | 10 | 98.99 | |||
20 | 98.75 | ||||
30 | 98.76 | ||||
40 | 99.13 | ||||
DOP | 10 | 98.67 | |||
20 | 98.99 | ||||
30 | 98.56 | ||||
40 | 98.89 | ||||
X-A method | TpBD COFs | DMP | 10 | 98.26 | |
20 | 98.53 | ||||
30 | 98.42 | ||||
40 | 98.21 | ||||
DEP | 10 | 98.10 | |||
20 | 98.76 | ||||
30 | 98.52 | ||||
40 | 98.00 | ||||
DBP | 10 | 98.99 | |||
20 | 98.23 | ||||
30 | 98.41 | ||||
40 | 97.93 | ||||
DOP | 10 | 98.08 | |||
20 | 98.76 | ||||
30 | 99.23 | ||||
40 | 98.45 | ||||
Resin based COFs | DMP | 10 | 98.60 | ||
20 | 98.61 | ||||
30 | 98.48 | ||||
40 | 98.67 | ||||
DEP | 10 | 98.58 | |||
20 | 98.49 | ||||
30 | 98.26 | ||||
40 | 98.00 | ||||
DBP | 10 | 98.99 | |||
20 | 98.56 | ||||
30 | 98.70 | ||||
40 | 98.23 | ||||
DOP | 10 | 98.06 | |||
20 | 98.88 | ||||
30 | 98.31 | ||||
40 | 98.16 |
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Ma, Y.; Gao, X.; Ruan, Y.; Cui, H.; Zhang, L.; Zhang, W.; Wang, S. Determination of Phthalate Esters in Beverages and Water Samples by Solid Phase Extraction with Resin Based COFs as Filler. Water 2021, 13, 3338. https://doi.org/10.3390/w13233338
Ma Y, Gao X, Ruan Y, Cui H, Zhang L, Zhang W, Wang S. Determination of Phthalate Esters in Beverages and Water Samples by Solid Phase Extraction with Resin Based COFs as Filler. Water. 2021; 13(23):3338. https://doi.org/10.3390/w13233338
Chicago/Turabian StyleMa, Yunjie, Xin Gao, Yang Ruan, Hang Cui, Li Zhang, Wei Zhang, and Shaoyan Wang. 2021. "Determination of Phthalate Esters in Beverages and Water Samples by Solid Phase Extraction with Resin Based COFs as Filler" Water 13, no. 23: 3338. https://doi.org/10.3390/w13233338