SUPPLEMENTARY DATA. Waste-to-useful: Biowaste-derived heterogeneous catalyst for a green and sustainable Henry reaction
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1 Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 209 SUPPLEMENTARY DATA Waste-to-useful: Biowaste-derived heterogeneous catalyst for a green and sustainable Henry reaction Kalyani Rajkumari, Diparjun Das, Gunindra Pathak and Lalthazuala Rokhum * Department of Chemistry, National Institute of Technology Silchar, Silchar-0, Assam, India * Corresponding author. Tel.: ; fax: ; address: lalthazualarokhum@gmail.com; rokhum@che.nits.ac.in (L. Rokhum) Table of Contents XRF data of metallic and non-metallic concentration in recovered MAPA catalyst (Table S) 2 XPS survey and deconvulated spectra of Recovered MAPA catalyst (Fig: S) 3 EDX spectra and TEM-SEM images of the recovered MAPA catalyst (Fig: S2, S3) 4 Calculation of Atom economy and E-factor 5 Spectral data H NMR and 3 C NMR Spectra of 2-nitro--(4-nitrophenyl)ethanol (3a) H NMR and 3 C NMR Spectra of 2-Nitro--(2-nitrophenyl)ethan--ol (3c) H NMR and 3 C NMR Spectra of 2-nitro--(3-nitrophenyl)ethanol (3d) H NMR and 3 C NMR Spectra of -(4-Fluorophenyl)-2-nitroethan--ol (3e) H NMR and 3 C NMR Spectra of -(4-Chlorophenyl)-2-nitroethan--ol (3f) H NMR and 3 C NMR Spectra of -(4-Bromophenyl)-2-nitroethan--ol (3g) H NMR and 3 C NMR Spectra of -(4-methoxyphenyl)-2-nitroethan--ol (3h) H NMR and 3 C NMR Spectra of 2-nitro--(3,4,5-trimethoxyphenyl)ethan--ol (3j) H NMR and 3 C NMR Spectra of 2-Nitro--(p-tolyl)ethan--ol (3k) H NMR and 3 C NMR Spectra of -Nitropentan-2-ol (3l) H NMR and 3 C NMR Spectra of 6-((tert-butyldimethylsilyl)oxy)--nitrohexan-2-ol (3m)
2 H NMR and 3 C NMR Spectra of 2-Nitro--(4-nitrophenyl)propan--ol (3o) H NMR and 3 C NMR Spectra of 2-Nitro--(3-nitrophenyl)propan--ol (3p) H NMR and 3 C NMR Spectra of -(4-Chlorophenyl)-2-nitropropan--ol (3q) H NMR and 3 C NMR Spectra of 4-(-Hydroxy-2-nitropropyl)benzonitrile (3r) H NMR and 3 C NMR Spectra of -(2-Bromophenyl)-2-nitropropan--ol (3s) H NMR and 3 C NMR Spectra of 2-Nitro--(p-tolyl)propan--ol (3t) H NMR and 3 C NMR Spectra of 2-nitrohexan-3-ol (3u) H NMR and 3 C NMR Spectra of 5,9-Dimethyl-2-nitrodec-8-en-3-ol (3v) H NMR and 3 C NMR Spectra of 2-nitro-7-((tetrahydro-2H-pyran-2-yl)oxy)heptan-3-ol (3w)- 34 Table S: Metallic and non-metallic concentration in recovered MAPA after 0 th recyclability test as given by XRF analysis. Sl No Name of the % Mass fraction in fresh % Mass fraction in component in the MAPA recovered MAPA MAPA sample after 0 th recycles.. K 2 O SiO CaO P 2 O SO MgO Fe 2 O Al 2 O MnO CuO
3 Fig: S a) XPS survey spectrum, b) Cs, c) Os, d) K2p spectra of recovered MAPA. 3
4 Fig. S2: EDS analysis of the recovered catalyst (after 0 th cycle). Fig S3: a-b) TEM and b-c) SEM images of the recycled catalyst. 4
5 Calculation of Atom Economy and E-factor: Atom economy= = Mass of atoms in desired product Mass of atoms in reactant 0.22g ( )g 00% = 00% Total waste (g) E-factor = Product (g) Mass in the process= Aldehyde + Nitroalkane + Catalyst = ( ) g = g Product = g Total waste = ( ) g = g g E-factor = g = 0.5 Spectral data: 2-Nitro--phenylethanol (Table 4, entry 3a) 3a 5
6 Colorless oil, H NMR (400 MHz, CDCl 3 ): δ 2.68 (s, H), δ (m, 2H), δ (m, H), δ (m, 5H). 3 C NMR (00 MHz, CDCl 3 ): δ 73.08, 77.7, 3.65, 7.63, 27.4, 35.08; IR (KBr pellet, ν max /cm - ): 3429, 308, 2408, 553, 433, 22, 035, 963, 777, nitro--(4-nitrophenyl)ethan--ol (Table 4, entry 3b) O 2 N 3b Brown solid, H NMR (CDCl 3, 400 MHz): δ 3.62 (H, s), δ 4.6 (2H, d, J= 40 Hz), δ 5.62(H, m), δ 7.6 (2H,d, J=8Hz), δ 8.2 (2H, d, J=7.6 Hz); 3 C NMR (CDCl 3, 25 MHz): δ 69.98, 80.67, 24.3, 27.0, 45.3, 47.95; IR (KBr pellet, ν max /cm - ): 3320, 3075, 2965, 2885, 608,532, 508, 430, 358, 320, 2, 058, 765, Nitro--(2-nitrophenyl)ethan--ol (Table 4, entry 3c) 3c Oily liquid, H NMR (CDCl 3, 400 MHz): δ (m, H), δ 4.87 (H, d, J=3.6 Hz), δ 6.05 (H, d, J=9.2 Hz), δ 7.56 (H, t, J= 8Hz), δ 7.97 (H, d, J=7.6), δ 8.07 (H, d, J=8Hz), δ 8.3 (H, d, J=7.6 Hz), 3C-NMR (00 MHz, CDCl3, TMS): d 34.37, 34.6, 33.8, 3.3, 29.64, 28.77, 24.95, 66.79; IR (KBr pellet, ν max /cm - ): ν 3305, 3025, 2939, 2889, 2787, 553, 432, 379, 323, 28, 78, 2,
7 2-nitro--(3-nitrophenyl)ethanol (3d) O 2 N 3d Yellow solid, H NMR (CDCl 3, 400 MHz): δ.25 (H, s), δ (2H, m), δ (H, m), δ7.6 (H, t, J=8 Hz), δ7.79 (H, d, J=8 Hz), δ8.9 (H, d, J=8 Hz), δ8.3 (H, s); 3 C NMR (CDCl 3, 25 MHz): δ 69.84, 80.7, 2.4, 23.77, 30.4, 32.5, 40.35, 48.45; IR (KBr pellet, ν max /cm - ): ν 3304, 3075, 2956, 2870, 62,545, 5, 437, 368, 329, 095, 058, 775, (4-Fluorophenyl)-2-nitroethan--ol (3e) F 3e Light yellow liquid, H NMR (CDCl 3, 400 MHz): δ 2.92 (H, s), δ (H, m), δ (H, m), δ 4.78 (H, t, J=6.8 Hz), δ (m, H), δ 7.2 (2H, d, J=8.4 Hz), (H, dd, J=8 Hz), δ (H, dd, J= 8 Hz); 3C-NMR (00 MHz, CDCl 3, TMS): δ 6.66, 33.86, 27.74, 6.4, 5.93, 70.32; IR (KBr pellet, ν max /cm - ): ν 3425, 302, 2909, 200, 704, 526, 32, 879, (4-Chlorophenyl)-2-nitroethan--ol (3f) Cl 3f 7
8 Colorless liquid, H NMR (CDCl 3, 400 MHz): δ 2.57 (H, s), δ 4.56 (H, d, J= 3.6Hz), δ 4.80 (H, t, J= 7.2 Hz), δ (H, m), δ 7.8 (2H, d, J=8.4 Hz), δ 7.35 (H, d, J=8.4 Hz); 3 C-NMR (00 MHz, CDCl 3, TMS): δ 70.29, 27.37, 29.8, 28.80, 32.67, 38.37; IR (KBr, ν max /cm - ): 3408, 3035, 2979, 2989, 2756, 536, 428, 389, 326, 275, 85, 5, 840, (4-Bromophenyl)-2-nitroethan--ol (3g) Br 3g Pale yellow oil, H NMR (CDCl 3, 400 MHz): δ 2.03 (H, s), δ (H, m), δ 4.79 (H, t, J= 7.2 Hz), δ (H, m), δ 7.29 (2H, d, J=8.4 Hz), δ 7.54 (H, d, J=8.4 Hz); 3 C-NMR (00 MHz, CDCl 3, TMS): δ 70.33, 22.89, 27.68, 29.2, 32.4, 38.05; IR (KBr pellet, ν max /cm - ): ν345, 3025, 2939, 2889, 2787, 550, 440, 38, 33, 280, 84, 20, (4-methoxyphenyl)-2-nitroethan--ol (3h) MeO 3h Yellow liquid, H NMR (CDCl 3, 400 MHz): δ 2.92 (H, s), δ 3.80 (3H, s), δ 4.46 (H, d, J=2.4 Hz) ; δ 4.58 (H, t, J=0 Hz), δ 5.382(H,d, J=8 Hz), δ 6.90 (2H, d, J= 7.6 Hz), δ 7.30 (2H, d, J=7.2 Hz); 3 C NMR (CDCl 3, 25 MHz): δ 55.35, 70.65, 80.26, 4.35, 27.3, 28.55, 30.55, 59.96; IR (KBr pellet, ν max /cm - ): 3378, 3083, 2943, 2896, 2780, 62, 536, 425, 82, 050, 790,
9 2-nitro--(3,4,5-trimethoxyphenyl)ethan--ol (3j) MeO MeO OMe 3j Brown solid, H NMR (CDCl 3, 400 MHz): δ.25 (H, s), δ 3.82 (3H, s), δ 3.86 (6H, s), δ (2H, m), δ (H, m), δ 6.60 (2H, s); 3 C NMR (CDCl 3, 25 MHz): δ 56.3, 60.85, 8.33, 02.69, 33.97, , 53.58; IR (KBr pellet, ν max /cm - ): 3308, 3025, 2960, 2856, 2775, 608, 556, 423, 0, 043, Nitro--(p-tolyl)ethan--ol (3k) 3k Light yellow oil, H NMR (CDCl 3, 400 MHz): δ.52 (H, s), 2.34 (3H, s), δ (H, m), δ (H, m), δ (H, m), δ (H, dd, J=7.6Hz); 3 C-NMR (00 MHz, CDCl 3, TMS): δ 2.6,70.90, 25.89, 29.67, 29.93, 38.89, 39.04;IR (KBr pellet, ν max /cm - ): ν 3429, 308, 2408, 553, 433, 22, 035, 963, 777, Nitropentan-2-ol (3l) 3l 9
10 Yellow liquid, H NMR (CDCl 3, 400 MHz): δ 0.96 (H, t, J=6.4 Hz), δ (H, s), 3.9 (H, s), 3.9 (H, s), (2H, m); 3 C-NMR (00 MHz, CDCl 3, TMS): δ 5.95, 8.89, 35.4, 65.9, 86.47; IR (KBr pellet, ν max /cm - ): 336, 2846, 64, 520, 206, 7, 853, ((tert-butyldimethylsilyl)oxy)--nitrohexan-2-ol (3m) TBSO 3m Colorless oil; H-NMR (400 MHz, CDCl 3, TMS): δ 0.26 (6H,s),δ 0.83 (9H, s), δ (6H, m), δ (H, m), δ 3.89 (2H, t, J ¼ 7.2 Hz), δ (H, m), δ (H, m), δ 5.25 (H, s); 3C-NMR (00 MHz, CDCl3, TMS): d 80.60, 68.58, 62.83, 36.0, 33.35, 32.3, 25.95, 2.66, 5.3; IR (KBr pellet, ν max /cm - ): 753, 628, 528, 20,9, 865, 769, Nitro--(4-nitrophenyl)propan--ol (3o) O 2 N 3o Reddish liquid, H NMR (CDCl 3, 400 MHz): δ (H, dd, J=6.8 Hz), δ (2H, dd, J=6.8 Hz), δ3.26 (H, s), δ (H, m), δ 5.2 (H, d, J= 8.4 Hz), δ7.62 (2H, d, J= 4.8 Hz), δ (H, dd, J=4 Hz), δ (H, dd, J=4.4 Hz); 3 C-NMR (00 MHz, CDCl 3, TMS): δ 6.6, 75.03, 87.88, 24.36, 28.0, 47.7, 48.; IR (KBr pellet, ν max /cm - ): ν 3435, 3330, 3025, 2889, 2789, 547, 440, 320, 284, 223, Nitro--(3-nitrophenyl)propan--ol (3p) 0
11 O 2 N 3p Reddish liquid, H NMR (CDCl 3, 400 MHz): δ (.5H, dd, J=6 Hz), δ (.5H, dd, J=6 Hz), δ (H, m), δ 5.22 (H, d, J= 8.4 Hz), δ (H, dd, J= 8.4 Hz), δ 7.78 (H, d, J=7.6 Hz), δ 8.50 (H, d, J=7.6 Hz) 8.69 (H, s); 3 C-NMR (00 MHz, CDCl 3, TMS): δ 6., 74.97, 88.0, 2.95, 23.84, 33.2, 35.00, 40.83, 48.38; IR (KBr, pellet, ν max /cm - ): 3445, 330, 3055, 289, 2779,536, 44, 327, 282, 242, 58. -(4-Chlorophenyl)-2-nitropropan--ol (3q) Cl 3q Colorless oil, H NMR (CDCl 3, 400 MHz): δ.47 (3H, d, J=6.8 Hz), δ (H, m), δ 5.0 (H, d, J= 8.8 Hz), δ7.52 (2H, d, J= 7.6 Hz), δ 7.8 (2H, d, J=7.6 Hz); 3 C-NMR (00 MHz, CDCl3, TMS): δ 6.33, 3.77, 88.25, 27.40, 28.32, 3.47, 36.87; IR (KBr pellet, ν max /cm - ): 340, 3025, 2949, 2889, 2786, 546, 438, 38, 323, 28, 79, 2, 845, (-Hydroxy-2-nitropropyl)benzonitrile (3r) NC 3r Light green liquid, H NMR (CDCl 3, 400 MHz): δ (.5 H, d, J=6.8 Hz), δ (.5 H, dd, J=6.8 Hz), δ (H, m), δ 5.2 (H, d, J= 8.8 Hz), δ7.86 (2H, d, J= 8 Hz), δ 8.0
12 (2H, d, J=8 Hz); 3 C-NMR (00 MHz, CDCl3, TMS): δ 5.95, 73.3, 87.93, 2.07, 8.32, 26.97, 32.57, 43.87; IR (KBr pellet, ν max /cm - ): 3555, 3059, 294, 2055, 976, 528, 448, 280, (2-Bromophenyl)-2-nitropropan--ol (3s) Br 3s Yellow liquid, H NMR (CDCl 3, 400 MHz): δ (.5 H, dd, J=4 Hz), δ (.5 H, dd, J=6.8 Hz), δ (H, m), δ 5.55 (H, d, J= 6.8 Hz), δ 5.75 (H, s), δ7.2 (H, t, J= 5.2 Hz), δ 7.45 (H, d, J=6.8 Hz), δ 7.55 (H, t, J=7.2 Hz), δ 7.59 (H, d, J=7.6 Hz); 3 C-NMR (00 MHz, CDCl3, TMS): δ 6.0, 73.9, 88.33, 2.53, 29.94, 30.32, 32.32, 37.98; IR (KBr pellet, ν max /cm - ): 335, 2957, 2863, 2756, 527, 379, Nitro--(p-tolyl)propan--ol (3t) 3t Colorless liquid, H NMR (CDCl 3, 400 MHz): δ (.5 H, dd, J=6 Hz), δ (.5 H, dd, J=6 Hz), δ (H, m), δ 5.22 (H, d, J= 8.4 Hz), δ 5.56 (H, s), δ (H, dd, J= 8.4 Hz), δ 7.78 (H, d, J=7.6 Hz), δ 8.69 (H,s); 3 C-NMR (00 MHz, CDCl 3, TMS): δ 6., 74.97, 88.0, 2.53, 29.95, 23.84, 33.2, 35.00, 40.38, 48.83; IR (KBr pellet, pellet, ν max /cm - ): ν 3445, 330, 3055, 289, 2779, 536, 44, 327, 282, 242, 58. 2
13 2-nitrohexan-3-ol (3u) 3u Light yellow liquid, H NMR (CDCl 3, 400 MHz): δ (3H, m), δ (4H, m), δ (3H, d, J=4.4), δ 2.69 (H, s), δ (H, m), δ (H, m); 3 C NMR (CDCl 3, 25 MHz): δ 3.74, 6.2, 8.35, 34.9, 7.8, 86.4; IR (KBr pellet, ν max /cm - ): 3306, 2946, 2830, 608, 536, 206, 48, 035, 838, ,9-Dimethyl-2-nitrodec-8-en-3-ol (3v) 3v Colorless liquid, H NMR (CDCl 3, 400 MHz): δ 0.93 (3H, d, J=6.8 Hz), δ 0.96 (3H, dd, J=6.4 Hz), δ.54 (6H, t, J=6.4 Hz), δ (8H, m), δ.60 (6H,s), δ.68 (6H,s), δ (2H, m), δ (4H, m), δ (H, m), δ (H, m), δ (H, m), δ (H, m), δ (2H, m), δ (2H, m); 3 C-NMR (00 MHz, CDCl 3, TMS): δ 0., 0.2, 7.6, 8.6, 8.7, 20.0, 20.3, 25.4, 25.9, 25.3, 25.7, 28.4, 25.7, 28.6, 28.8, 29., 35.7, 36., 37.6, 37.8, 40., 40.4, , 70.8, 7., 86.8, 87.9, 88.4, 24.3, 3.5, 3.6; IR (KBr pellet, ν max /cm - ): 3540, 3025, 2925, 620, 553, 454, 38, nitro-7-((tetrahydro-2H-pyran-2-yl)oxy)heptan-3-ol (3w) THPO 3w 3
14 Light yellow liquid, H NMR (CDCl 3, 400 MHz): δ (3H, m), δ 2.5 (H, s), δ (2H, m), δ (H, m),δ (2H,m), δ (H, m), δ (H, m); 3 C-NMR (00 MHz, CDCl 3, TMS): δ 0., 0.2, 7.6, 8.6, 8.7, 20.0, 20.3, 25.4, 25.9, 25.3, 25.7, 28.4, 25.7, 28.6, 28.8, 29., 35.7, 36., 37.6, 37.8, 40., 40.4, , 70.8, 7., 86.8, 87.9, 88.4, 24.3, 3.5, 3.6; IR (KBr pellet, ν max /cm - ): 330, 306, 2940, 656, 530, 403, 350, 80, 875, 76. 4
15 O 2 N O 2 N 3a Fig: S4 : H NMR and 3 C NMR Spectra of 2-nitro--(4-nitrophenyl)ethanol (Table 3, Entry 3a) 5
16 3c 3c Fig S5: H NMR and 3 C NMR Spectra of 2-Nitro--(2-nitrophenyl)ethan--ol (Table 3, Entry 3c) 6
17 O 2 N 3d O 2 N Fig S6: H NMR and 3 C NMR Spectra of 2-nitro--(3-nitrophenyl)ethanol (Table 3, Entry 3d) 7
18 F 3e F 3e Fig S7: H NMR and 3 C NMR Spectra of -(4-Fluorophenyl)-2-nitroethan--ol (Table 3, Entry 3e) 8
19 Cl 3f Cl Fig S8:- H NMR and 3 C NMR Spectra of -(4-Chlorophenyl)-2-nitroethan--ol (Table 3, Entry 3f) 9
20 Br 3g Br 3g Fig S9: H NMR and 3 C NMR Spectra of -(4-Bromophenyl)-2-nitroethan--ol (Table 3, Entry 3g) 20
21 MeO 3h MeO 3h Fig S0: H NMR and 3 C NMR Spectra of -(4-methoxyphenyl)-2-nitroethan--ol (Table 3, Entry 3h) 2
22 MeO MeO OMe 3j MeO MeO OMe 3j Fig S: H NMR and 3 C NMR Spectra of -(3, 4-Dimethoxyphenyl)-2-nitroethanol (Table 3, Entry 3j) 22
23 3k 3k Fig S2: H NMR and 3 C NMR Spectra of 2-Nitro--(p-tolyl)ethan--ol (Table 3, Entry 3k) 23
24 3l 3l Fig S3: H NMR and 3 C NMR Spectra of -Nitropentan-2-ol (Table 3, Entry 3l) 24
25 TBSO 3m TBSO 3m Fig S4: H NMR and 3 C NMR Spectra of 6-((tert-butyldimethylsilyl)oxy)--nitrohexan-2-ol (Table 3, Entry 3m) 25
26 O 2 N 3o O 2 N 3o Fig S5 : H NMR and 3 C NMR Spectra of 2-Nitro--(4-nitrophenyl)propan--ol (Table 3, Entry 3o) 26
27 O 2 N 3p O 2 N 3p Fig S6 : H NMR and 3 C NMR Spectra of 2-Nitro--(3-nitrophenyl)propan--ol (Table 3, Entry 3p) 27
28 Cl 3q Cl 3q Fig S7 : H NMR and 3 C NMR Spectra of -(4-Chlorophenyl)-2-nitropropan--ol (Table 3, Entry 3q) 28
29 NC 3r NC 3r Fig S 8: H NMR and 3 C NMR Spectra of 4-(-Hydroxy-2-nitropropyl)benzonitrile (Table 3, Entry 3r) 29
30 Br Br Fig S9 : H NMR and 3 C NMR Spectra of -(2-Bromophenyl)-2-nitropropan--ol (Table 3, Entry) 30
31 3t 3t Fig S20 : H NMR and 3 C NMR Spectra of 2-Nitro--(p-tolyl)propan--ol (Table 3, Entry 3t) 3
32 3u 3u Fig S 2 : H NMR and 3 C NMR Spectra of 2-nitrohexan-3-ol (Table 3, Entry 3u) 32
33 3v 3v Fig S 22 : H NMR and 3 C NMR Spectra of 5,9-Dimethyl-2-nitrodec-8-en-3-ol (Table 3, Entry) 33
34 THPO 3w THPO 3w Fig S 23 : H NMR and 3 C NMR Spectra of 2-nitro-7-((tetrahydro-2H-pyran-2-yl)oxy)heptan-3-ol (Table 3, Entry 3w) 34
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