Synthesis of Hindered Phenolic Esters over Ion-Exchange Resins
Supporting Information for
Synthesis of Hindered Phenolic Esters over Ion-Exchange Resins Wensheng Gao1, Ying Feng1, Yanyan Huang1, Ligong Chen1,2, Xilong Yan1,2* 1
School of Chemical Engineering and Technology, Tianjin University, Tianjin, P.R. China
2
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, P.R.
China E-mail: [email protected] S1. General information of experiment The ion-exchange resins (NKC-9, D072, D001-CC, D001-SS, 001×4, 001×7, 001×14.5, D113), HY and γ-Al2O3 were obtained from the Chemical Plant of Nankai University (China) and the main parameters of the sulphonic acid functionalized resins were shown in Table S1. These catalysts were used after they have been dried under vacuum at 333 K for 48 h. Other chemicals were purchased from commercial suppliers and used without further purification unless otherwise noted. HPLC were used to monitor the esterification. HPLC analyses were performed on a Agilent 1100 Series instrument at ambient temperature using Zorbaz Eclipse XDB-C18 column (reverse phase, 4.6 mm × 250 mm, 5-Micron), mobile phase: 90% methanol and aqueous acetic acid(0.5%, W/W). Column chromatography was performed using 200-300 mesh silica gel (Qingdao Haiyang). 1
H NMR and
13
C NMR spectra were recorded on Bruker AVANCE III 600MHz NMR
spectrometer, using TMS as an internal standard. High-resolution mass spectra were measured with a Bruker Daltonics micrOTOF-Q II instrument (ESI). Elemental Analysis data were measured using an Elementar Vario Micro cube instrument.
Table S1 Main parameters of sulphonic acid functionalized resinsa. Catalystb
Structure
Acidity
SBET c
The ratio of
Pore volume 3
Average pore
(mmol/g)
2
(m /g)
acidity and SBET
(cm /g)
diameter (nm)
Tmax(℃)
NKC-9
MR
4.8
11.94
0.40
0.030
10.09
100
D072
MR
4.4
15.79
0.28
0.044
11.03
120
D001-CC
MR
4.1
22.86
0.18
0.073
12.82
120
D001-SS
MR
4.2
-
-
-
-
120
001×4
G
4.5
-
-
-
-
120
001×7
G
4.5
-
-
-
-
120
001×14.5
G
3.8
-
-
-
-
120
MR: macroporous structure. G: gel type polymer. a
Date taken from reference[1].
b
The particle size of ion-exchange resins is 0.3-1.25 mm.
c
The acidity of dry ion-exchange resins was detected.
S2. 1H and 13C NMR information of products： hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate[2]
1
H NMR (CDCl3, 600 MHz): δ = 0.88(t, JHH= 6.6Hz, 3H, CH3), 1.25-1.43 (m, 26H, C13H26),
1.46(s, 18H, 2C(CH3)3), 1.75(m, 2H, CH2) 4.27(t, JHH = 6.6Hz, 2H, COOCH2), 5.64(s, 1H, OH), 7.9 (s, 2H; ArH). 13
C NMR (CDCl3, 150 MHz): δ =14.13, 22.71, 26.11, 28.85, 29.32, 29.39, 29.60, 29.72, 30.16,
31.95, 34.33, 64.68, 121.60, 127.00, 135.67, 158.05, 167.21 ppm. Elemental Analysis: Anal. Calcd for C31H54O3: C, 78.43; H, 11.46; O, 10.11. Found: C, 78.44; H, 11.43; O, 10.13. HRMS (ESI Positive) calc. for C31H54O3, [M+H]+ 475.4146, found 475.4146 .
100 50 14.128
1.0
26.107 22.709
2.0
31.951 30.163 29.721 29.602 29.387 29.322 28.848
3.0
34.332
64.679
77.251 77.040 76.828
121.597
126.996
135.669
158.051
167.212
4.0 2.99
5.0 26.18 18.23
150 6.0 2.13
7.0 2.09
ppm (t1) 1.00
2.00
8.0 ppm (t1)
0
1.255 0.890 0.879 0.867
1.364 1.354 1.341 1.330 1.319 1.296
1.768 1.757 1.745 1.733 1.721 1.548 1.461 1.431 1.418 1.406
4.284 4.273 4.262
5.642
7.260
7.900
300000000
250000000
200000000
150000000
100000000
50000000
0
0.0
400000000
300000000
200000000
100000000
0
tetradecyl 3,5-di-tert-butyl-4-hydroxybenzoate
1
H NMR (CDCl3，600 MHz): δ = 0.88(t, JHH= 6.6Hz, 3H, CH3), 1.25-1.43(m, 22H, C11H22), 1.46(s,
18H, 2C(CH3)3), 1.74(m, 2H, CH2), 4.28(t, JHH = 6.6Hz, 2H, COOCH2), 5.65(s, 1H, OH), 7.91(s, 2H; ArH). 13
C NMR (CDCl3, 150 MHz): δ =14.13, 22.71, 26.11, 28.85, 29.32, 29.38, 29.60, 29.71, 30.16,
31.95, 34.33, 64.69, 121.59, 127.00, 135.68, 158.06, 167.24 ppm. Elemental Analysis: Anal. Calcd for C29H50O3: C, 77.97; H, 11.28; O, 10.74. Found: C, 77.82; H, 11.29; O, 10.89.
1.257 0.891 0.880 0.868
1.308 1.296
1.364 1.355 1.342
1.769 1.758 1.746 1.734 1.722 1.547 1.461 1.431 1.426 1.419 1.407
4.285 4.274 4.263
5.643
7.260
7.901
HRMS (ESI Positive) calc. for C29H50O3, [M+H]+ 447.3833, found 447.3833.
150000000
100000000
50000000
0
4.0
3.0
2.0
3.15
5.0
22.26 18.05
6.0
2.11
7.0
2.01
1.00
2.00
8.0 ppm (t1)
1.0
0.0
14.128
26.106 22.708
31.947 30.162 29.702 29.599 29.379 29.318 28.847
34.333
64.692
77.257 77.045 76.833
121.585
127.000
135.678
158.063
167.236
250000000
200000000
150000000
100000000
50000000
0
150
100
50
ppm (t1)
octyl 3,5-di-tert-butyl-4-hydroxybenzoate
1
H NMR (CDCl3, 600 MHz): δ = 0.88(t, JHH= 6.6Hz, 3H, CH3), 1.28-1.44(m, 10H, C5H10), 1.46(s,
18H, 2C(CH3)3), 1.74(m, 2H, CH2), 4.28(t, JHH = 6.6Hz, 2H, COOCH2), 5.65(s, 1H, OH), 7.90(s, 2H; ArH).
13
C NMR (CDCl3, 150 MHz): δ =14.10, 22.67, 26.10, 28.84, 29.25, 30.16, 31.79, 34.34, 64.69,
121.58, 127.00, 135.69, 158.07, 167.24 ppm. Elemental Analysis: Anal. Calcd for C23H38O3: C, 76.20; H, 10.56; O, 13.24. Found: C, 76.11; H, 10.60; O, 13.28.
0.892 0.881 0.869
1.369 1.365 1.355 1.343 1.332 1.316 1.305 1.294 1.284
1.771 1.760 1.748 1.735 1.724 1.549 1.461 1.435 1.425 1.422
4.286 4.275 4.264
5.643
7.260
7.901
HRMS (ESI Positive) calc. for C23H38O3, [M+H]+ 363.2894, found 363.2894.
60000000
50000000
40000000
30000000
20000000
10000000
0
14.103
26.101 22.666
29.251 28.841
0.0
31.794 30.161
1.0
34.338
2.0
64.686
3.0
77.271 77.060 76.848
121.582
127.000
135.693
158.074
167.240
4.0
2.98
5.0
10.07 18.19
6.0
2.06
7.0
2.12
1.02
2.00
8.0 ppm (t1)
250000000
200000000
150000000
100000000
50000000
0
150 ppm (t1)
100
50
hexadecyl 3-(tert-butyl)-4-hydroxybenzoate[3]
1
H NMR (CDCl3, 600 MHz): δ = 0.88(t, JHH= 7.2Hz, 3H, CH3), 1.25-1.41(m, 26H, C13H26), 1.42(s,
9H, C(CH3)3), 1.75(m, 2H, CH2), 4.28(t, JHH = 6.6Hz, 2H, COOCH2), 5.70 (s, 1H, OH), 6.71(d, JHH = 7.8, 1H, ArH), 7.78 (dd, JHH = 1.8 and 8.4 Hz, 1H, ArH), 8.00(d, JHH =1.8 Hz, 1H, ArH). 13
C NMR (CDCl3, 150 MHz): δ =14.13, 22.71, 26.08, 28.79, 29.32, 29.36, 29.61, 29.68, 29.72,
31.95, 34.67, 65.11, 116.36, 121.99, 129.25, 136.17, 159.29, 167.7 ppm. Elemental Analysis: Anal. Calcd for C27H46O3: C, 77.46; H, 11.07; O, 11.46. Found: C, 77.41; H, 11.09; O, 11.49. HRMS (ESI Positive) calc. for C27H46O3, [M+H]+ 419.3520, found 419.3521.
100 50 14.131
26.075 22.709
1.0
29.719 29.683 29.605 29.358 29.316 28.788
2.0
31.948
3.0
34.673
65.109
77.245 77.034 76.822
116.359
121.983
129.246
136.166
159.288
4.0 2.97
5.0 25.98 9.14
6.0 0.67 2.08
7.0 2.02
150 0.99
8.0 ppm (t1) 1.01
ppm (t1) 0.99
1.00
167.700
0.892 0.880 0.868
1.360 1.349 1.336 1.324 1.297 1.285 1.276 1.257
1.423 1.404
1.643
1.772 1.761 1.749 1.736 1.725
4.294 4.283 4.272
5.696
6.720 6.707
7.792 7.789 7.778 7.775 7.260
8.006 8.003
200000000
150000000
100000000
50000000
0
0.0
350000000
300000000
250000000
200000000
150000000
100000000
50000000
0
-50000000
hexadecyl 4-hydroxybenzoate[3]
1
H NMR (CDCl3, 600MHz): δ =0.86(t, JHH= 7.2Hz, 3H, CH3), 1.25-1.46(m, 26H, C13H26), 1.74(m,
2H, CH2), 4.28 (t, JHH = 6.6Hz, 2H, COOCH2), 5.47 (s, 1H, OH), 6.86 (dd, JHH = 2.4 and 7.2 Hz, 2H; ArH), 7.96 (dd, JHH = 3 and 9.6 Hz, 2H; ArH). 13
C NMR (CDCl3, 150 MHz): δ =14.13, 22.70, 26.06, 28.74, 29.31, 29.38, 29.55, 29.61, 29.67,
29.71, 31.94, 65.26, 115.31, 122.47, 131.93, 160.43, 167.26 ppm. Elemental Analysis: Anal. Calcd for C23H38O3: C, 76.20; H, 10.56; O, 13.24. Found: C, 76.22; H, 10.60; O, 13.18.
1.354 1.344 1.331 1.318 1.307 1.296 1.274 1.256 0.891 0.879 0.867
1.458 1.455 1.448 1.437 1.427 1.412 1.400
1.768 1.757 1.745 1.732 1.721 1.710 1.602
4.290 4.279 4.268
5.466
6.866 6.862 6.854 6.851
7.260
7.971 7.966 7.955 7.952
HRMS (ESI Positive) calc. for C23H38O3, [M+Na]+ 385.2713, found 385.2711.
350000000
300000000
250000000
200000000
150000000
100000000
50000000
0
3.0
2.0
3.02
4.0
22.00 4.03
5.0
2.15
6.0
2.18
7.0
0.98
2.03
2.00
8.0 ppm (t1)
-50000000 1.0
0.0
-1.0
14.125
26.057 22.703
28.738
29.710 29.671 29.606 29.550 29.378 29.308
31.940
65.261
77.245 77.033 76.821
115.305
122.473
131.930
160.433
167.264
400000000
300000000
200000000
100000000
0
150
100
50
ppm (t1)
Reference [1] Wang, W.; Wei, R.; Yin, G.; Tian, J.; Duan, Y.; Chen, L.; Li, Y. The synthesis of asymmetric ethylenediamine derivatives catalyzed by ion-exchange resins. Res. Chem. Intermediat. 2014, 1-12. [2] Jordan, S.; Taylor, L. HPLC separation with solvent elimination FTIR detection of polymer additives. J. chromatogr. sci. 1997, 35, 7-13. [3] Ohkatsu, Y.; Takenaka, H.; Kamiyama, N. Interaction of Benzoate-type Ultraviolet Absorbers with Hindered Amine Light Stabilizers. J. Jpn. Petrol. Inst. 2008, 51, 95-101.
Synthesis of Hindered Phenolic Esters over Ion-Exchange Resins Wensheng Gao1, Ying Feng1, Yanyan Huang1, Ligong Chen1,2, Xilong Yan1,2* 1
School of Chemical Engineering and Technology, Tianjin University, Tianjin, P.R. China
2
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, P.R.
China E-mail: [email protected] S1. General information of experiment The ion-exchange resins (NKC-9, D072, D001-CC, D001-SS, 001×4, 001×7, 001×14.5, D113), HY and γ-Al2O3 were obtained from the Chemical Plant of Nankai University (China) and the main parameters of the sulphonic acid functionalized resins were shown in Table S1. These catalysts were used after they have been dried under vacuum at 333 K for 48 h. Other chemicals were purchased from commercial suppliers and used without further purification unless otherwise noted. HPLC were used to monitor the esterification. HPLC analyses were performed on a Agilent 1100 Series instrument at ambient temperature using Zorbaz Eclipse XDB-C18 column (reverse phase, 4.6 mm × 250 mm, 5-Micron), mobile phase: 90% methanol and aqueous acetic acid(0.5%, W/W). Column chromatography was performed using 200-300 mesh silica gel (Qingdao Haiyang). 1
H NMR and
13
C NMR spectra were recorded on Bruker AVANCE III 600MHz NMR
spectrometer, using TMS as an internal standard. High-resolution mass spectra were measured with a Bruker Daltonics micrOTOF-Q II instrument (ESI). Elemental Analysis data were measured using an Elementar Vario Micro cube instrument.
Table S1 Main parameters of sulphonic acid functionalized resinsa. Catalystb
Structure
Acidity
SBET c
The ratio of
Pore volume 3
Average pore
(mmol/g)
2
(m /g)
acidity and SBET
(cm /g)
diameter (nm)
Tmax(℃)
NKC-9
MR
4.8
11.94
0.40
0.030
10.09
100
D072
MR
4.4
15.79
0.28
0.044
11.03
120
D001-CC
MR
4.1
22.86
0.18
0.073
12.82
120
D001-SS
MR
4.2
-
-
-
-
120
001×4
G
4.5
-
-
-
-
120
001×7
G
4.5
-
-
-
-
120
001×14.5
G
3.8
-
-
-
-
120
MR: macroporous structure. G: gel type polymer. a
Date taken from reference[1].
b
The particle size of ion-exchange resins is 0.3-1.25 mm.
c
The acidity of dry ion-exchange resins was detected.
S2. 1H and 13C NMR information of products： hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate[2]
1
H NMR (CDCl3, 600 MHz): δ = 0.88(t, JHH= 6.6Hz, 3H, CH3), 1.25-1.43 (m, 26H, C13H26),
1.46(s, 18H, 2C(CH3)3), 1.75(m, 2H, CH2) 4.27(t, JHH = 6.6Hz, 2H, COOCH2), 5.64(s, 1H, OH), 7.9 (s, 2H; ArH). 13
C NMR (CDCl3, 150 MHz): δ =14.13, 22.71, 26.11, 28.85, 29.32, 29.39, 29.60, 29.72, 30.16,
31.95, 34.33, 64.68, 121.60, 127.00, 135.67, 158.05, 167.21 ppm. Elemental Analysis: Anal. Calcd for C31H54O3: C, 78.43; H, 11.46; O, 10.11. Found: C, 78.44; H, 11.43; O, 10.13. HRMS (ESI Positive) calc. for C31H54O3, [M+H]+ 475.4146, found 475.4146 .
100 50 14.128
1.0
26.107 22.709
2.0
31.951 30.163 29.721 29.602 29.387 29.322 28.848
3.0
34.332
64.679
77.251 77.040 76.828
121.597
126.996
135.669
158.051
167.212
4.0 2.99
5.0 26.18 18.23
150 6.0 2.13
7.0 2.09
ppm (t1) 1.00
2.00
8.0 ppm (t1)
0
1.255 0.890 0.879 0.867
1.364 1.354 1.341 1.330 1.319 1.296
1.768 1.757 1.745 1.733 1.721 1.548 1.461 1.431 1.418 1.406
4.284 4.273 4.262
5.642
7.260
7.900
300000000
250000000
200000000
150000000
100000000
50000000
0
0.0
400000000
300000000
200000000
100000000
0
tetradecyl 3,5-di-tert-butyl-4-hydroxybenzoate
1
H NMR (CDCl3，600 MHz): δ = 0.88(t, JHH= 6.6Hz, 3H, CH3), 1.25-1.43(m, 22H, C11H22), 1.46(s,
18H, 2C(CH3)3), 1.74(m, 2H, CH2), 4.28(t, JHH = 6.6Hz, 2H, COOCH2), 5.65(s, 1H, OH), 7.91(s, 2H; ArH). 13
C NMR (CDCl3, 150 MHz): δ =14.13, 22.71, 26.11, 28.85, 29.32, 29.38, 29.60, 29.71, 30.16,
31.95, 34.33, 64.69, 121.59, 127.00, 135.68, 158.06, 167.24 ppm. Elemental Analysis: Anal. Calcd for C29H50O3: C, 77.97; H, 11.28; O, 10.74. Found: C, 77.82; H, 11.29; O, 10.89.
1.257 0.891 0.880 0.868
1.308 1.296
1.364 1.355 1.342
1.769 1.758 1.746 1.734 1.722 1.547 1.461 1.431 1.426 1.419 1.407
4.285 4.274 4.263
5.643
7.260
7.901
HRMS (ESI Positive) calc. for C29H50O3, [M+H]+ 447.3833, found 447.3833.
150000000
100000000
50000000
0
4.0
3.0
2.0
3.15
5.0
22.26 18.05
6.0
2.11
7.0
2.01
1.00
2.00
8.0 ppm (t1)
1.0
0.0
14.128
26.106 22.708
31.947 30.162 29.702 29.599 29.379 29.318 28.847
34.333
64.692
77.257 77.045 76.833
121.585
127.000
135.678
158.063
167.236
250000000
200000000
150000000
100000000
50000000
0
150
100
50
ppm (t1)
octyl 3,5-di-tert-butyl-4-hydroxybenzoate
1
H NMR (CDCl3, 600 MHz): δ = 0.88(t, JHH= 6.6Hz, 3H, CH3), 1.28-1.44(m, 10H, C5H10), 1.46(s,
18H, 2C(CH3)3), 1.74(m, 2H, CH2), 4.28(t, JHH = 6.6Hz, 2H, COOCH2), 5.65(s, 1H, OH), 7.90(s, 2H; ArH).
13
C NMR (CDCl3, 150 MHz): δ =14.10, 22.67, 26.10, 28.84, 29.25, 30.16, 31.79, 34.34, 64.69,
121.58, 127.00, 135.69, 158.07, 167.24 ppm. Elemental Analysis: Anal. Calcd for C23H38O3: C, 76.20; H, 10.56; O, 13.24. Found: C, 76.11; H, 10.60; O, 13.28.
0.892 0.881 0.869
1.369 1.365 1.355 1.343 1.332 1.316 1.305 1.294 1.284
1.771 1.760 1.748 1.735 1.724 1.549 1.461 1.435 1.425 1.422
4.286 4.275 4.264
5.643
7.260
7.901
HRMS (ESI Positive) calc. for C23H38O3, [M+H]+ 363.2894, found 363.2894.
60000000
50000000
40000000
30000000
20000000
10000000
0
14.103
26.101 22.666
29.251 28.841
0.0
31.794 30.161
1.0
34.338
2.0
64.686
3.0
77.271 77.060 76.848
121.582
127.000
135.693
158.074
167.240
4.0
2.98
5.0
10.07 18.19
6.0
2.06
7.0
2.12
1.02
2.00
8.0 ppm (t1)
250000000
200000000
150000000
100000000
50000000
0
150 ppm (t1)
100
50
hexadecyl 3-(tert-butyl)-4-hydroxybenzoate[3]
1
H NMR (CDCl3, 600 MHz): δ = 0.88(t, JHH= 7.2Hz, 3H, CH3), 1.25-1.41(m, 26H, C13H26), 1.42(s,
9H, C(CH3)3), 1.75(m, 2H, CH2), 4.28(t, JHH = 6.6Hz, 2H, COOCH2), 5.70 (s, 1H, OH), 6.71(d, JHH = 7.8, 1H, ArH), 7.78 (dd, JHH = 1.8 and 8.4 Hz, 1H, ArH), 8.00(d, JHH =1.8 Hz, 1H, ArH). 13
C NMR (CDCl3, 150 MHz): δ =14.13, 22.71, 26.08, 28.79, 29.32, 29.36, 29.61, 29.68, 29.72,
31.95, 34.67, 65.11, 116.36, 121.99, 129.25, 136.17, 159.29, 167.7 ppm. Elemental Analysis: Anal. Calcd for C27H46O3: C, 77.46; H, 11.07; O, 11.46. Found: C, 77.41; H, 11.09; O, 11.49. HRMS (ESI Positive) calc. for C27H46O3, [M+H]+ 419.3520, found 419.3521.
100 50 14.131
26.075 22.709
1.0
29.719 29.683 29.605 29.358 29.316 28.788
2.0
31.948
3.0
34.673
65.109
77.245 77.034 76.822
116.359
121.983
129.246
136.166
159.288
4.0 2.97
5.0 25.98 9.14
6.0 0.67 2.08
7.0 2.02
150 0.99
8.0 ppm (t1) 1.01
ppm (t1) 0.99
1.00
167.700
0.892 0.880 0.868
1.360 1.349 1.336 1.324 1.297 1.285 1.276 1.257
1.423 1.404
1.643
1.772 1.761 1.749 1.736 1.725
4.294 4.283 4.272
5.696
6.720 6.707
7.792 7.789 7.778 7.775 7.260
8.006 8.003
200000000
150000000
100000000
50000000
0
0.0
350000000
300000000
250000000
200000000
150000000
100000000
50000000
0
-50000000
hexadecyl 4-hydroxybenzoate[3]
1
H NMR (CDCl3, 600MHz): δ =0.86(t, JHH= 7.2Hz, 3H, CH3), 1.25-1.46(m, 26H, C13H26), 1.74(m,
2H, CH2), 4.28 (t, JHH = 6.6Hz, 2H, COOCH2), 5.47 (s, 1H, OH), 6.86 (dd, JHH = 2.4 and 7.2 Hz, 2H; ArH), 7.96 (dd, JHH = 3 and 9.6 Hz, 2H; ArH). 13
C NMR (CDCl3, 150 MHz): δ =14.13, 22.70, 26.06, 28.74, 29.31, 29.38, 29.55, 29.61, 29.67,
29.71, 31.94, 65.26, 115.31, 122.47, 131.93, 160.43, 167.26 ppm. Elemental Analysis: Anal. Calcd for C23H38O3: C, 76.20; H, 10.56; O, 13.24. Found: C, 76.22; H, 10.60; O, 13.18.
1.354 1.344 1.331 1.318 1.307 1.296 1.274 1.256 0.891 0.879 0.867
1.458 1.455 1.448 1.437 1.427 1.412 1.400
1.768 1.757 1.745 1.732 1.721 1.710 1.602
4.290 4.279 4.268
5.466
6.866 6.862 6.854 6.851
7.260
7.971 7.966 7.955 7.952
HRMS (ESI Positive) calc. for C23H38O3, [M+Na]+ 385.2713, found 385.2711.
350000000
300000000
250000000
200000000
150000000
100000000
50000000
0
3.0
2.0
3.02
4.0
22.00 4.03
5.0
2.15
6.0
2.18
7.0
0.98
2.03
2.00
8.0 ppm (t1)
-50000000 1.0
0.0
-1.0
14.125
26.057 22.703
28.738
29.710 29.671 29.606 29.550 29.378 29.308
31.940
65.261
77.245 77.033 76.821
115.305
122.473
131.930
160.433
167.264
400000000
300000000
200000000
100000000
0
150
100
50
ppm (t1)
Reference [1] Wang, W.; Wei, R.; Yin, G.; Tian, J.; Duan, Y.; Chen, L.; Li, Y. The synthesis of asymmetric ethylenediamine derivatives catalyzed by ion-exchange resins. Res. Chem. Intermediat. 2014, 1-12. [2] Jordan, S.; Taylor, L. HPLC separation with solvent elimination FTIR detection of polymer additives. J. chromatogr. sci. 1997, 35, 7-13. [3] Ohkatsu, Y.; Takenaka, H.; Kamiyama, N. Interaction of Benzoate-type Ultraviolet Absorbers with Hindered Amine Light Stabilizers. J. Jpn. Petrol. Inst. 2008, 51, 95-101.
